Antifungal carbinols

ABSTRACT

Antifungal carbinols, particularly α-styryl carbinols, and the corresponding epoxy carbinols are provided. These carbinol compounds have the formula: ##STR1## or a pharmaceutically or agriculturally suitable salt thereof wherein E is a bond or an oxygen atom with the proviso that when E is oxygen; R, R 1  are not halogen; and 
     L, A, B, Q, R 2 , R 3 , R 4  and n are as defined in the specification.

CROSS-REFERENCE

This is a division of application Ser. No. 07/423,243, filed Oct. 18,1989, now U.S. Pat. No. 4,980,367, which is a division of applicationSer. No 07/134,261, filed Dec. 17, 1987, now U.S. Pat. No. 4,922,232which is a continuation-in-part of application Ser No. 42,541, filedApr. 29, 1987 (now abandoned, which in turn is a continuation-in-part ofapplication Ser. No. 877,525, filed Jun. 23, 1986 (now abandoned).

FIELD OF THE INVENTION

This invention relates to antifungal carbinols, particularly α-styrylcarbinols, and the corresponding epoxy carbinols, pharmaceutical andagricultural compositions containing them, processes for preparing themand methods of using them as antifungal agents in mammals and plants.

BACKGROUND INCLUDING PRIOR ART

Systemic fungal infections are of increasing importance because ofcontinued and expanded use of immunosuppressive therapies, antimicrobialtherapies and indwelling catheters. Currently there are limitedtherapies available to treat such fungal infections. Amphotericin Bremains the drug of choice because it has the widest spectrum ofantifungal activity of any systemic antifungal drug, however its utilityis limited by its toxicity. Because of the potential seriousness of itstoxic effects, intravenous use of amphotericin B is primarily forpatients with progressive, potentially fatal infections in which thepatient is hospitalized during the course of therapy. Thus, there is acontinuing need to develop safer and more effective drugs which areuseful for the treatment of fungal infections.

Plant pathogenic fungi and other disease incitants also cause extensivelosses in crops annually. While there are commercially availablematerials used to control many plant diseases, further improvement inthis art is needed if full food and fiber production is to be realized.

There are a large number of patent and literature references in the areaof azole antifungal drugs and plant disease control agents. Mostpertinent to the α-styryl carbinol compounds of this invention are thefollowing references:

B. Sugavanam in U.S. Pat. No. 4,507,140 issued Mar. 26, 1985 disclosesfungicidal or plant growth regulating β-styryl triasoles or imidazoles,amongst others of the formula: ##STR2## wherein R¹ is CH═CH--X;--C.tbd.C--X or --CH₂ --CH₂ --X;

X is substituted aryl, aralkyl, or heterocycle;

R² is alkyl, cycloalkyl, or optionally substituted aryl;

Z is OR³ ;

R³ is H, acetyl;

Y is --N-- or --CH--.

German Patent 3,018,865, published May 16, 1980 discloses antimycoticagents of the formula: ##STR3## where amongst others R is alkyl,optionally substituted cycloalkyl or optionally substituted phenylradical;

X is N, or a CH group;

X is --OCH₂ --, --CH₂ CH₂ -- or CH═CH;

Z is halogen, alkyl, cycloalkyl, alkoxy, alkythio, etc.

German Patent 3,314,548-A, published Apr. 21, 1983 discloses substituted1-hydroxy-ethyl-triazole derivatives of the formula: ##STR4## whereamongst others R is alkyl, cycloalkyl or phenyl optionally substituted;

X is --OCH₂ --, --SCH₂ --, --(CH₂)_(p) or --CH═CH--;

Z is halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, orhaloalkylthio;

m and p are 0, 1 and 2.

The compounds ar antimycotics of treating dermatophytomycoses andsystemic nycoses caused, e.g., by Candida sp., Aspergillus sp.,Trichophyton sp.

The above three references, which pertain to β-styryl azoles, arebelieved to be the most relevant. The β-styryl azole analog of one ofthe preferred compounds of the instant invention was prepared and foundto be significantly less active.

European Patent Application 114,487 which published Aug. 1, 1984discloses azolylethanol derivatives of the formula: ##STR5##

Where amongst others R¹ and R² which may be the same or different arehydrogen, alkyl, cycloalkyl, alkenyl, heterocyclyl aryl, or aralkyloptionally substituted; W is N or CH; and X is C═O. The compounds havefungicidal activity and plant growth regulating activity.

European Patent No. 117,578-A, published Feb. 23, 1984 disclosesheterocyclic-hydroxy-alkyl alkyl ketone(s) and analogues of the formula:##STR6## where A is CO amongst others;

Q is imidazoyl or 1H- or 4H-1,2,4-triazol-1-yl;

R¹ is H, 1-5C alkyl, or 1-8C acyl;

R² and R³ are 1-5C alkyl, 3-6C cycloalkyl, 2-6C alkenyl, benzyl(optionally substituted by 1-3 halogen), pyridyl, furyl, thienyl, orphenyl optionally substituted by 1-3 halogen, 1-3 alkyl, or 1-3C alkoxy.

Belgian Patent 900,594-A published Sept. 22, 1983 discloses1-phenyl-1-azolyl-hydroxyethyl cycloalkane derivatives of the formula:##STR7## where R₁ and R₂ =H, halo, NO₂, lower alkyl, alkenyl, alkynyl,alkoxy or alkylthio (all optionally substituted by 1 or more halo), oroptionally substituted phenyl or phenoxy;

R₃ =H or lower alkyl;

R₄ and R₅ =H or halo;

Y=CH or N;

A=2-7C alkylene;

n=0 or 1.

The compounds are useful as agricultural fungicides and antimycotics.

None of the cited references nor any known references suggest the novelantifungal compounds of this invention.

SUMMARY OF THE INVENTION

According to the present invention compounds are provided having theformula: ##STR8## or a pharmaceutically or agriculturally suitable saltthereof wherein E is a bond or an oxygen atom with the proviso that whenE is oxygen; R, R¹ are not halogen;

A is perfluoralkyl of 1-8 carbon atoms N(CH₃)₂, OH, naphthyl optionallysubstituted with a total of 1-3 substituents each of which isindependently selected from halogen and CF₃, ##STR9## optionallysubstituted with 1 or 2 methyl groups, phenyl optionally substitutedwith a total of 1-3 substituents each of which is independently selectedfrom:

Halogen, alkyl of 1-4 carbon atoms, haloalkyl of 1-4 carbon atoms,alkoxy of 1-4 carbon atoms, and with no more than one group selectedfrom: haloalkoxy of 1-4 carbon atoms, CN, CO₂ E₁₄, CH═NOR₁₄, S(O)_(m)R⁵, R₆, 2-,3-, or 4-pyridyl or an N-oxide thereof, imidazol-1-yl,1,2,4-triazol-1-yl, and ##STR10## optionally substituted with 1 or 2methyl groups, or a heterocycle selected from imidazol-1-yl,1,2,4-triazol-1-yl, 2-or 3-thienyl, and 2-,3-, or 4-pyridyl or anN-oxide thereof, optionally substituted with one or two substituentseach of which in independently selected from:

halogen, alkyl of 1-4 carbon atoms, CF₃, alkoxy of 1-4 carbon atoms,haloalkoxy of 1-4 carbon atoms, and S(O)_(m) R⁵ ;

B is alkyl of 1-8 carbon atoms, naphthyl, biphenyl, ##STR11##perfluoroalkyl of 1-8 carbon atoms, phenyl optionally substituted with1-3 substituents each of which is independently selected from: halogen,alkyl of 1-4 carbon atoms, haloalkyl of 1-4 carbon atoms, alkoxy of 1-4carbon atoms, and with no more than one group selected from haloalkoxyof 1-4 carbon atoms, CN, CO₂ R₁₄, CH═NOR₁₄, S(O)_(m) R⁵, 2-,3-,4-Pyridyl or an N oxide thereof,

benzyl optionally substituted on the phenyl ring with halogen or alkylof 1-4 carbon atoms, or optionally α-substituted with 1 or 2 methylgroups, or

a heterocycle selected from 2-or 3-thienyl, and 2-,3-,or 4-pyridyl, saidheterocycles being optionally substituted with one or two substituentseach of which is independently selected from:

halogen, alkyl of 1-4 carbon atoms, haloalkoxy of 1-4 carbon atoms, CF₃,or S(O)_(m) R⁵ ;

Q is H, halogen, S(O)_(m) R¹¹, ##STR12## CO₂ R¹³, SCN, SSR¹², or SH orits corresponding disulfide, provided however that when Q is other thanH, then n is O, R, R¹, and R⁴ are independently H or CH₃, R³ is H, and Aand B are each phenyl optionally substituted with from 1-3 substitutedeach of which is independently halogen, CH₃, CF₃, OCH₃, or S(O)_(m) R⁵ ;

L is CH or N with the proviso that when L=CH then Q=H;

n is 0-4 with the proviso that when A is ##STR13## N(CH₃)₂, or OH, thenn is other than O; m each occurrence is 0, 1 or 2;

X is C, NR¹⁰, or O;

R and R¹ independently are H, alkyl of 1-4 carbon atoms, halogen, orphenyl, or taken together form cycloalkyl of 3-7 carbon atoms;

R² is H, allyl, propargyl, alkyl of 1-4 carbon atoms, ##STR14## orhaloalkyl of 1-4 carbon atoms; R³ and R⁴ independently are H, F, oralkyl or 1-4 carbon atoms;

R⁵ is alkyl of 1-4 carbon atoms;

R⁶ is phenyl optionally substituted with a total of 1-3 substituentseach of which is independently selected from halogen and CF₃ ;

R⁷ is alkyl of 1-4 carbon atoms, phenyl, or benzyl;

R⁸ and R⁹ independently are H, alkyl of 1-4 carbon atoms, phenyl orbenzyl;

R¹⁰ is H, alkyl of 1-4 carbon atoms, or acetyl;

R¹¹ is alkyl of 1-4 carbon atoms, haloalkyl of 1-2 carbon atoms, CH₂ CN,CH₂ SCN, CH(CH₃)CN, CH₂ CO₂ CH₃, or CH₂ CO₂ CH₂ CH₃ ;

R¹² is alkyl of 1-4 carbon atoms, allyl, phenyl optionally substitutedwith 1-2 substituents each of which is independently halogen, CH₃, orOCH₃, or benzyl optionally substituted with 1-2 substituents each ofwhich is independently halogen, CH₃, or OCH₃ ;

R¹³ is H, or alkyl of 1-4 carbon atoms; and

R¹⁴ is alkyl of 1-4 carbon atoms.

Also provided are pharmaceutical compositions comprising a suitablepharmaceutical carrier and a therapeutically effective amount of acompound of Formula (I) or its pharmaceutically suitable salt andmethods of using the compounds of Formula (I) as antifungal agents.

This invention further provides agricultural compositions comprising acompound of Formula (I) or its agriculturally suitable salt togetherwith an agriculturally acceptable diluent or carrier and a method ofcontrolling fungal diseases in plants.

Certain compounds of this invention are useful as herbicides and plantgrowth regulants. This invention, therefore, also relates to theherbicidal compositions of these compounds and their method of use asherbicides.

The herbicidal compounds are those of Formula (I) wherein:

E is a bond;

L is N;

A is perfluoralkyl of 1-4 carbon atoms, naphthyl optionally substitutedwith a total of 1-2 substituents each of which is independently selectedfrom halogen and CF₃, ##STR15## optionally substituted with 1 or 2methyl groups, phenyl optionally substituted with a total of 1-3substituents each of which is independently selected from:

halogen, alkyl of 1-3 carbon atoms, haloalkyl of 1-3 carbon atoms,alkoxy of 1-3 carbon atoms, and with no more than one group selectedfrom:

haloalkoxy of 1-3 carbon atoms, CN, CO₂ R¹⁴, CH═NOR¹⁴, R₆, 2-,3-, or4-pyridyl, or an N-oxide thereof, imidazol-1-yl, 1,2,4-triazol-1-yl, and##STR16## optionally substituted with 1 or 2 methyl groups, or aheterocycle selected from imidazol-1-yl, 1,2,4-triazol-1-yl, 2-or3-thienyl, and 2-,3-, or 4-pyridyl, said heterocycles being optionallysubstituted with one or two substituents each of which is independentlyselected from:

halogen, alkyl of 1-2 carbon atoms, and CF₃ ;

B is alkyl of 1-4 carbon atoms, naphthyl, perfluoroalkyl of 1-4 carbonatoms, phenyl optionally substituted with 1-2 substituents each of whichis independently selected from: halogen, alkyl of 1-3 carbon atoms,haloalkyl of 1-3 carbon atoms, alkoxy of 1-3 carbon atoms, and with nomore than one group selected from haloalkoxy of 1-3 carbon atoms, andCN,

benzyl optionally substituted on the phenyl ring with halogen or alkylof 1-3 carbon atoms, or optionally α-substituted with 1 or 2 methylgroups, or

a heterocycle selected from 2-or 3-thienyl, and 2-,3-,or 4-pyridyl, saidheterocycles being optionally substituted with one or two substituentseach of which is independently selected from:

halogen, alkyl of 1-3 carbon atoms, or CF₃ ;

Q is H, halogen, S(O)_(m) R¹¹, ##STR17## CO₂ R¹³, SCN, SSR¹², or SH orits corresponding disulfide, provided however that when Q is other thanH, then n is O, R, R¹, and R⁴ are independently H or CH₃, R³ is H, and Aand B are each phenyl optionally substituted with from 1-3 substituentseach of which is independently halogen, CH₃, CF₃, or OCH₃ ;

n is 0-2 with the proviso that when A is ##STR18## then n is other thanO; m each occurrence is 0, 1 or 2;

X is C, NR¹⁰, or O;

R and R¹ independently are H, alkyl of 1-2 carbon atoms, halogen, orphenyl, or taken together form cycloalkyl of 3-6 carbon atoms;

R² is H, allyl, propargyl, alkyl of 1-2 carbon atoms, ##STR19## orhaloalkyl of 1-4 carbon atoms; R³ and R⁴ independently are H, F, oralkyl of 1-2 carbon atoms;

R⁶ is phenyl optionally substituted with a total of 1-3 substituentseach of which is independently selected from halogen and CF₃ ;

R⁷ is alkyl of 1-2 carbon atoms, phenyl, or benzyl;

R⁸ and R⁹ independently are H, alkyl of 1-2 carbon atoms, phenyl orbenzyl;

R¹⁰ is H, alkyl or 1-2 carbon atoms, or acetyl;

R¹¹ is alkyl of 1-2 carbon atoms, haloalkyl of 1-2 carbon atoms, CH₂ CN,CH₂ SCN, CH(CH₃)CN, CH₂ CO₂ CH₃, or CH₂ CO₂ CH₂ CH₃ ;

R¹² is alkyl of 1-2 carbon atoms, allyl, phenyl optionally substitutedwith 1-2 substituents each of which is independently halogen, CH₃, orOCH₃, or benzyl optionally substituted with 1-2 substituents each ofwhich is independently halogen, CH₃, or OCH₃ ; and

R¹³ is H, or alkyl of 1-2 carbon atoms.

Further provided are processes for the preparation of the aforesaidcompounds, which processes are described hereinafter.

Additionally provided are novel intermediates having the formulas (II)and (IIa) shown below: ##STR20## wherein A, B, R, R¹, R³, R⁴ and n areas defined above, except that R³, R⁴ are not F and not both alkyl.

REFERRED EMBODIMENTS

Preferred compounds are the α-styryl compounds of formula (I) (E is abond) where:

1) n=0, or 1; and/or

2) R³ and R⁴ independently are H, CH₃ or F.

More preferred compounds are preferred compounds where:

1) A, and B independently are phenyl optionally substituted with from1-3 substituents each of which is halogen, alkyl of 1-4 carbon atoms,haloalkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, or S(O)_(m)R⁵ ; and/or

2) n=O; and/or

3) R and R¹ independently are H, CH₃ or halogen; and/or

4) R² =H, alkyl of 1-4 carbon atoms, allyl, or propargyl; and/or

5) Q is H, I, SH.

Most preferred compounds are more preferred compounds where:

1) A and B independently are phenyl optionally substituted with from 1-3halogen atoms, CH₃, OCH₃, CF₃, or SCH₃ ; and/or;

2) R, R¹, R², R³, R⁴ and Q are all H.

Specifically preferred because of their biological activity are thefollowing compounds or salts thereof:

(a) 2-(4-Fluorophenyl)-3-phenyl-1-(1H, 1,2,4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(b) 2,3-Bis(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; andthe (S) enantiomer thereof.

(c)2-(2,4-Dichlorophenyl)-3-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(d)2-(4-Chlorophenyl)-3-(2-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(e)2-(2,4-Dichlorophenyl)-3-(3-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(f)2-(2-Chlorophenyl)-3-(2-chlorophenyl)-1-(1H-1,2,4-triasol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(g)2-(2,4-Dichlorophenyl)-3-(3-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-S-buten-2-ol;and the (S) enantiomer thereof.

(h)2-(4-Fluorophenyl)-3-(4-trifluoromethyl-phenyl)-1-(1H-1,2,4-triazol-1yl)-3-buten-2-ol;and the (S) enantimoer thereof.

(i)2-(2,4-Dichlorophenyl)-3-phenyl-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(j)2-(3,4-Dichlorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2-4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(k)2-(4-Chlorophenyl)-3-(3-chlorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(l)2-(4-Fluorophenyl)-3-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(m)2-(2,4-Difluorophenyl)-3-(2-chlorophenyl)-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(n)2-(2,4-Dichlorophenyl)-3-(2-chlorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(o) 2-(2,4-Difluorophenyl)-3-phenyl)-1-(1H-imidazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(p)2-(2,4-Difluorophenyl)-3-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(q)2-(2,4-Difluorophenyl)-3-(2-chlorophenyl)-1-(1H-imidazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(r)2-(2,4-Difluorophenyl)-3-phenyl-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(s)2-(2,4-Difluorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(t)2-(2-Fluorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(u)2-(2-Fluorophenyl)-3-(4-chlorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(v)2-(2,4-Difluorophenyl)-3-(4-chlorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(w)2-(2-Chlorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

(x) 2-(4-Chlorophenyl)-3-phenyl-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol;and the (S) enantiomer thereof.

All of the compounds within the scope of this invention are active ineither pharmaceutical or agricultural fungicidal assays. Thus, it shouldbe recognized that there are compounds which are not always active inboth assays as is shown with some compounds in the Examples. Of theabove listed specifically preferred compounds, compounds (a)-(r) ortheir salts are preferred for pharmaceutical uses and compounds (r)-(x)or their salts are preferred for agricultural uses.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The novel compounds of Formula (I) can be prepared using the reactionsand techniques described in this section. The reactions are usuallyperformed in a solvent appropriate to the reagents and materialsemployed, and suitable for the transformation being effected. In somecases functional groups on the starting materials may need to beprotected by standard protecting groups reported in the chemicalliterature which are well known to one skilled in the art.

In some cases, substituents on the starting materials may beincompatible with some of the reaction conditions required in some ofthe methods described. Such restrictions to the substituents which arecompatible with the reaction conditions will be readily apparent to oneskilled in the art and alternative methods described must then be used.

The compounds of the present invention can contain at least one chiralcenter and as such can exist as two individual isomers or as a racemicmixture of both. This invention relates to the (S) isomer, as well as toracemic mixtures containing both isomers.

For the purposes of this invention, the (S)-isomer of compounds ofFormula (I) is intended to mean compounds of the configuration depicted:##STR21##

When a single chiral center is present the resolution can be performedby reacting the compound with a chiral strong acid (e.g. substitutedcamphor-sulfonic acids) in a suitable solvent (e.g. acetonitrile) ormixture of solvents (e.g. 3/1 etheracetone). This reaction is carriedout at a temperature between 25° C. to 100° C., preferably at the refluxtemperature of the solvent(s) employed. The reaction produces twodiastereomeric adducts that can be separated by fractionalcrystallisation. The adduct can then be cleaved in basic medium (e.g.sat. NaHCO₃, sat. Na₂ CO₃) to give the resolved product.

The compounds of Formula I, where E is a bond, R² and Q are H and R³, R⁴are not F and not both alkyl, can be prepared by contacting an oxiraneof Formula (II) or a halohydrin of Formula (IIa), or a mixture of (II)or (IIa) with imidazole or triazole or a corresponding alkali metal salt(preferably the Na⁺ or K⁺ salt) in a suitable solvent (Scheme I).##STR22##

When imidazole or triazole is used, an acid acceptor, such as potassiumcarbonate, sodium methoxide or sodium hydride, is added to the reactionmixture. Suitable inert solvents include polar, aprotic solvents such asdimethylformamide (DMF), dimethylsulfoxide (DMSO) and etheral solventssuch as tetrahydrofuran (THF). Non-polar solvents, such as toluene, maybe used if a phase transfer catalyst, such as tetrabutylammoniumbromide, is added. The reaction is carried out at a temperature in therange of 10° to 150° C., preferably from 50° to 120° C., for a period of0.25 to 24 hours. It is recognized that varying amounts of the4H-1,2,4-triazol-4-yl isomers of Formula (I) may be formed when triazoleis used in the above reaction. The isomers can be separated, if desired,using standard separation techniques, e.g., chromatography.

The 4H-1,2,4-triazol-4-yl isomers of Formula (I) can be converted to thecompounds of Formula (I) by isomerization with base as described in EP143384A2, or by heating with 2-100 mol % of oxiranes of Formula (II),halohydrins of Formula (IIa), reactive alkyl or benzyl bromides oriodides, such as benzyl bromide or methyl iodide, or commercial oxiranessuch as styrene oxide, at temperatures of 100°-200° C.; preferably, in apolar aprotic solvent such as DMF, or a non-polar solvent such as one ofthe xylenes.

The oxiranes of Formula (II) can be prepared using one or both of thefollowing methods; (Scheme 2). In the first, vinyl organometallicreagents, e.g., vinyl Grignard reagents, of Formula (III) are allowed toreact with haloketones of Formula (IV) in the presence of etherealsolvents, such as THF or diethyl ether, at a temperature ranging from-90° to 60° C., preferably -10° to 50° C., for 0.5 to 24 hours.Depending on the reaction conditions and the value of X in thehaloketones starting material (IV), the product may be an oxirane (II),a halohydrins (IIa) or a mixture of (II) and (IIa). If desired, thehalohydrins (IIa) may be converted to oxiranes (II) by treatment withbase, e.g., potassium hydride (KH), in a solvent such as THF. ##STR23##

In the second method, keto-oxiranes of formula (V) are olefinated with,for example, Wittig reagents, which provide epoxy-olefins of Formula(II).

Unsaturated ketones of Formula (VII) can be converted to expoxy-olefins(II) by treatment with dimethylsulfonium methylide. The enones (VII) canbe prepared by treatment of ketones of Formula (VI) with carbonylcompounds and appropriate catalysts (Scheme 3). ##STR24##

Unsaturated ketones of Formula (VIII) can be converted to epoxyketones(V) using basic hydrogen peroxide. Olefination of (V), as describedabove, provides epoxyolefins (II) (Scheme 4). ##STR25##

The vinyl organometallics of Formula (III) are prepared using standardprocedures from the corresponding chlorides, bromides or iodides. Thehaloolefins, the haloketones of Formula (IV), the ketooxiranes ofFormula (V) and the ketones of Formula (VI) are known, or can beprepared using methods known to one skilled in the art.

Compounds of Formula (I) can also be prepared by olefination of ketones(IX) with, for example, Wittig reagents (Scheme 5). Ketones of Formula(IX) where R², R³ and R⁴ =H are known (EP 117578A). ##STR26##

Compounds of general Formula (I) where R³ and/or R⁴ ≠H can be made asshown in Scheme 6 by reacting ketones of general Formula (X) with theappropriate organometallic reagent (e.g. Grignard reagent, organolithiumreagent). The ketones (X) are prepared by conventional methods from thecorresponding α-haloketones (IV) (see e.g. EP 0044605, UK 2099818A, UK146224, EP 1337718, and EP 0153803). ##STR27##

Compounds of Formula (I) where A=(heterocycle)-phenyl can be preparedfrom appropriately substituted precursors using the methods describedabove, or by using substitution reactions on (I) wherein A ishalophenyl. For example, compounds of Formula (I) where A is(pyridyl)phenyl can be prepared by treatment of (I), wherein A isbromophenyl or iodophenyl, with the appropriate pyridylstannanes in thepresence of palladium catalysts (see Tetrahedron Letters, 27, 4407,1986). Copper assisted displacement of halogen (Tetrahedron, 40, 1433,1984) with heterocyclic nucleophiles provides compounds of Formula (I)where A is for example 1-imidazolylphenyl.

In some cases, it may be desirable to begin with compounds of Formula I,wherein A is aminophenyl, and construct the heterocyclic ring usingX(CH₂ CH₂ Cl)₂ (see ES 8603-473-A).

The compounds of Formula (I) where Q≠H and L=N can be prepared as shownin Scheme 7. Metalation of (I), -═H with strong base provides the5-metalated triazoles (Ia) (See Heterocycles, 23, 1645-49, 1985). WhenR² is H, 2 equivalents of base are required. Typical conditions involvetreatment of a solution of (I) in THF at -70° with n-butyllithium for15-30 minutes. Where the metalated triazole (Ia) is less soluble than(I), the addition of co-solvents, such as dimethylpropyleneurea (DMPU)may be beneficial. ##STR28##

The treatment of (Ia) with electrophiles gives a wide variety of (I)where Q≠H. Electrophiles of relevance to the present invention includehalogenating agents, sulfur, disulfides, carbon dioxide, dimethylamidesand sulfur dioxide followed by alkyl halides. Subsequentfunctionalization, using methods known to one skilled in the art,provide other compounds of Formula (I) wherein Q≠H. For example, thetreatment of (I), where Q is SH with isocyanates or phthalimidosulfidesprovides thiocarbamates (I; ##STR29## or disulfides (I; Q=SSR¹²),respectively.

The compounds of general Formula (I) where E is oxygen can be preparedby oxidation of compounds of general Formula (I) where E is a bondprovided that R, R¹ ≠halogen using methods described in the literature(Scheme 8): ##STR30##

Suitable reagents which can effect this oxidation, depending on thenature of the substituents, include peracids such as m-chloroperbenzoicacid; hydroperoxides such as tert-butyl hydroperoxide in the presence ofan appropriate catalyst such as vanadium acetonylacetonate; or hydrogenperoxide. Alternatively, the transformation can be effected by firstforming the halohydrin with a hypohalous acid such as hypobromous acidand then reacting the intermediate halohydrin with a proton acceptorsuch as potassium tert-butoxide.

It will be noted by those skilled in the art that, depending on thenature of the compound to be oxidized, a mixture of diastereomers can beobtained. This can be controlled through selection of appropriateoxidation methods or, alternatively, the resulting mixture ofdiastereomers can be separated in a conventional manner (e.g.chromatography, fractional crystallization).

Compounds of Formula (I) where R² is H can be alkylated, acylated andcarbamoylated, using standard procedures, to prepare functionalderivatives of the alcohol moiety.

The compounds of this invention and their preparation can be understoodfurther by the following examples, but should not constitute alimitation thereof. In these examples, unless otherwise indicated, alltemperatures are in degrees centigrade and parts and percentages are byweight.

Nuclear magnetic resonance (nmr) spectra were obtained in CDCl₃solution, unless otherwise noted. Abbreviations for nmr spectra ares=singlet, d=doublet, t=triplet, q=quartet, m=multiplet; peak positionsare reported as parts per million downfield from tetramethylsilane.

EXAMPLE 1 PART A2-(4-Fluorophenyl)-2-[1-(4-fluorophenyl)-ethenyl]oxirane

PROCESS 1: Grignard Addition to an α-Haloketone

To a 25° solution of Grignard reagent prepared from 6.0 g (0.030 mol) of1-bromo-4'-fluorostyrene and 0.85 g (0.035 mol) of magnesium turnings in60 mL of THF was added a solution of 5.2 g (0.030 mol) of2-chloro-4'-fluoroacetophenone in 10 mL of THF. The solution was stirredfor 2 hours at 25°. Saturated aqueous NH₄ Cl (10 mL) was added, theaqueous layer was extracted with 1:1 Et₂ O/hexane and the combinedorganic layers were washed with brine, dried over MgSO₄ and evaporatedto give 10.2 g of an amber oil. Analysis by NMR (CDCl₃) indicated thatthe desired oxirane was the major product: δ3.1, 3.3 (two d, epoxideprotons; 5.5, 5.8 (two s, vinyl protons). The material was of sufficientpurity to be used in the next step.

PROCESS 2: Olefination of 2-(4-Fluorophenyl)-2-(4-fluorobenzoyl)oxirane

To a suspension of 4.3 g (0.012 mol) of methyltriphenylphosphoniumbromide in 15 mL of THF cooled to -70° was added 8.4 mL (0.013 mol) of1.55M n-butyllithium over 3 min., keeping the temperature at less than-55°. The resulting yellow suspension was allowed to warm to 0° over 10min, and was then treated with 2.6 g (0.010 mol) of2-(4-fluorophenyl)-2-(4-fluorobensoyl)oxirane in 5 mL of THF. Thelight-brown suspension was stirred for 6 hours at 25°. Standard workupgave 3.4 g of crude product which was flash chromatographed (Et₂ O) togive 1.7 g of the desired product, which was of suffcient purity to beused in the next step. NMR (CDCl₃) δ3.1 (d): 3.3 (d); 5.5 (s); 5.8 (s).

PART B 2,3-Bis (4-Fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol

A mixture of 10.2 g (0.040 mol) of crude2-(4-fluorophenyl)-2-[1-(4-fluorophenyl)ethenyl]oxirane and 7.0 g (0.065mol) of potassium triazole in 60 mL of DMF was heated at 60° overnight,then cooled and poured into 100 mL of 1:1 Et₂ O/nexanes. After washingthe organic layer three times with H₂ O and once with brine, aprecipitate formed in the organic layer. Filtering gave 4.8 g of a brownsolid which was recrystallized from 500 mL of cyclohexane to yield 2.5 gof a light-tan powder, mp 136°-137°: NMR (CDCl₃) δ1.7 (br s, OH); 4.7(q, 2H); 5.3 (s, 1H); 5.5 (s, 1H); 6.8-7.1 (m, 6H); 7.4 (m, 2H); 7.8 (s,1H); 7.9 (s, 1H); IR (nujol) 3120 (br), 1900, 1600, 1505, 1220, 1139,835 cm⁻¹.

The compounds shown in Table 1 were prepared or can be prepared by themethod described hereinabove.

In the tables, Ph means phenyl and substituted aryl groups areabbreviated, e.g., 4-F-Ph is 4-fluorophenyl, 2,4-Cl₂ -Ph is2,4-dichlorophenyl and 2-thienyl is thiophen-2-yl.

    TABLE 1      ##STR31##      Ex.          No. A B n R R.sup.1 R.sup.2 R.sup.3 R.sup.4 M.P. °C.       1 4-FPh 4-FPh 0 H H H H H 136-137           (HCl salt     182-184) 2 4-FPh 2,4-Cl.sub.2Ph 0 H H H H H 139-143 3 4-FPh 4-ClPh 0 H H     H H H (oil).sup.a 4 4-FPh 2,4-F.sub.2Ph 0 H H H H H 102-103.5 5 4-FPh     4-CF.sub.3Ph 0 H H H H H 6 4-FPh -n-C.sub.4 H.sub.9 0 H H H H H 72-73 7     4-FPh -n-C.sub.4 F.sub.9 0 H H H H H 8 2-FPh Ph 0 H H H H H 9 2-FPh     2-FPh 0 H H H H H 89-93 10 2-FPh 4-FPh 0 H H H H H (oil).sup.b 11 2-FPh     2,4-F.sub.2Ph 0 H H H H H 121-122 12 2-FPh 2-ClPh 0 H H H H H 13 2-FPh     4-ClPh 0 H H H H H 116-117 14 2-FPh 2,4-Cl.sub.2Ph 0 H H H H H 115-116     15 3-FPh 4-FPh 0 H H H H H 106-109 16 3-FPh 2,4-Cl.sub.2Ph 0 H H H H H     145-147 17 3-FPh 4-ClPh 0 H H H H H 101-102 18 3-FPh 2,4-F.sub.2Ph 0 H H     H H H 92-93 19 3-FPh 4-CF.sub.3Ph 0 H H H H H 20 3-FPh -n-C.sub.4     H.sub.9 0 H H H H H 21 3-FPh -n-C.sub.4 F.sub.9 0 H H H H H 22 3-FPh Ph     0 H H H H H 23 3-FPh 2-FPh 0 H H H H H 122-124 24 3-FPh 2-ClPh 0 H H H H     H 25 4-ClPh 4-FPh 0 H H H H H 110-115 26 4-ClPh 2,4-Cl.sub.2Ph 0 H H H H     H 89-91          (HCl salt          184-190) 27 4-ClPh 4-ClPh 0 H H H H     H 132-135 28 4-ClPh 2,4-F.sub.2Ph 0 H H H H H 124-125.5 29 4-ClPh     4-CF.sub.3Ph 0 H H H H H 30 4-ClPh -n-C.sub.4 H.sub.9 0 H H H H H 31     P     4-Clh -n-C.sub.4 F.sub.9 0 H H H H H 32 2-ClPh 4-FPh 0 H H H H H     (oil).sup.c 33 2-ClPh 2,4-Cl.sub.2Ph 0 H H H H H 150-152 (HCl salt     124-127) 34 2-ClPh 4-ClPh 0 H H H H H 153-154 HNO.sub.3 salt 138-141          (HCl salt H.sub.2 SO.sub.4 salt 180-182          175-180) H.sub.3     PO.sub.4 salt 158-160 35 2-ClPh 2,4-F.sub.2Ph 0 H H H H H 128-129     H.sub.2 SO.sub.4 salt 184-187          (HCl salt HNO.sub.3 salt 158-159             156-161) H.sub.3 PO.sub.4 salt 141-143 36 2-ClPh 4-CF.sub.3Ph 0     H H H H H 37 2-ClPh -n-C.sub.4 H.sub.9 0 H H H H H 38 2-ClPh -n-C.sub.4     F.sub.9 0 H H H H H 39 3-ClPh 4-FPh 0 H H H H H 95-96.5 40 3-ClPh     2,4-Cl.sub.2Ph 0 H H H H H 144-146 41 3-ClPh 4-Cl Ph 0 H H H H H 112-115     42 3-ClPh 2,4-F.sub.2Ph 0 H H H H H 115-116 43 3-ClPh 4-CF.sub.3Ph 0 H H     H H H 44 3-ClPh -n-C.sub.4 H.sub.9 0 H H H H H 45 3-ClPh -n-C.sub.4     F.sub.9 0 H H H H H 46 3-ClPh Ph 0 H H H H H 47 3-ClPh 2-FPh 0 H H H H H     91-93 48 3-ClPh 2-ClPh 0 H H H H H 49 Ph 4-FPh 0 H H H H H 125-126 50 Ph     2,4-Cl.sub.2Ph 0 H H H H H 117-120 51 Ph 4-ClPh 0 H H H H H 111 52 Ph     2,4-F.sub.2Ph 0 H H H H H 119.5-122          (HCl salt          152-154)     53 Ph 4-CF.sub.3Ph 0 H H H H H 54 Ph -n-C.sub.4 H.sub.9 0 H H H H H 55     Ph -n-C.sub.4 F.sub.9 0 H H H H H 56 2-CF.sub.3Ph Ph 0 H H H H H     (oil).sup.r 57 2-CF.sub.3Ph 2-FPh 0 H H H H H 127.5-130 58 2-CF.sub.3Ph     2-ClPh 0 H H H H H 152-156 59 3-CF.sub.3Ph Ph 0 H H H H H 101-103 60     3-CF.sub.3Ph 2-FPh 0 H H H H H (oil).sup.s 61 3-CF.sub.3Ph 2-ClPh 0 H H     H H H 101-104 62 4-CF.sub.3Ph Ph 0 H H H H H 63 4-CF.sub.3Ph 2-FPh 0 H H     H H H 64 4-CF.sub.3Ph 2-ClPh 0 H H H H H 65 4-CF.sub.3Ph 4-FPh 0 H H H H     H 152-154 66 4-CF.sub.3Ph 2,4-Cl.sub.2Ph 0 H H H H H (oil).sup.t 67     4-CF.sub.3Ph 4-ClPh 0 H H H H H 144-145 68 4-CF.sub.3Ph 2,4-F.sub.2Ph 0     H H H H H 69 4-CF.sub.3Ph 4-CF.sub.3Ph 0 H H H H H 70 4-CF.sub.3Ph     -n-C.sub.4 H.sub.9 0 H H H H H 71 4-CF.sub.3Ph -n-C.sub.4 F.sub.9 0 H H     H H H 72 2-BrPh Ph 0 H H H H H 73 2-BrPh 2-FPh 0 H H H H H 74 2-BrPh     4-FPh 0 H H H H H 75 2-BrPh 2,4-F.sub.2Ph 0 H H H H H 76 2-BrPh 2-ClPh 0     H H H H H 77 2-BrPh 4-ClPh 0 H H H H H 78 2-BrPh 2,4-Cl.sub.2Ph 0 H H H     H H 79 3-BrPh Ph 0 H H H H H 80 3-BrPh 2-FPh 0 H H H H H 81 3-BrPh     2-ClPh 0 H H H H H 82 4-BrPh Ph 0 H H H H H 83 4-BrPh 2-FPh 0 H H H H H     84 4-BrPh 2-ClPh 0 H H H H H 123-126 85 4-BrPh 4-FPh 0 H H H H H     (oil).sup.d 86 4-BrPh 2,4-Cl.sub. 2Ph 0 H H H H H 87 4-BrPh 4-ClPh 0 H H     H H H 145-148 88 4-BrPh 2,4-F.sub.2Ph 0 H H H H H 123-125 89 4-BrPh     4-CF.sub.3Ph 0 H H H H H 90 4-BrPh -n-C.sub.4 H.sub.9 0 H H H H H 91     P     4-Brh -n-C.sub.4 F.sub.9 0 H H H H H 92 2,4-F.sub.2Ph Ph 0 H H H H H 93     2,4-F.sub.2Ph 2-FPh 0 H H H H H 106-108 94 2,4-F.sub.2Ph 4-FPh 0 H H H H     H 100-103 95 2,4-F.sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 116-120 96 2,4-F.sub     .2Ph 2-ClPh 0 H H H H H 97 2,4-F.sub.2Ph 4-ClPh 0 H H H H H 98 2,4-F.sub.     2Ph 2,4-Cl.sub.2Ph 0 H H H H H 99 2,4-Cl.sub.2Ph 4-FPh 0 H H H H H     (oil).sup.e 100 2,4-Cl.sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 75- 78 101     2,4-Cl.sub.2Ph 4-ClPh 0 H H H H H 60-62 102 2,4-Cl.sub.2Ph 2,4-F.sub.2Ph     0 H H H H H 106-109 103 2,4-Cl.sub.2Ph 4-CF.sub.3Ph 0 H H H H H 104     2,4-Cl.sub.2Ph -n-C.sub.4 H.sub.9 0 H H H H H 105 2,4-Cl.sub.2Ph     -n-C.sub.4 F.sub.9 0 H H H H H 106 2,4-Cl.sub.2Ph Ph 0 H H H H H 45-54     107 2,4-Cl.sub.2Ph 2-FPh 0 H H H H H 68-73 108 2,4-Cl.sub.2Ph 2-ClPh 0 H     H H H H (oil).sup.u 109 3,4-Cl.sub.2Ph Ph 0 H H H H H 110 3,4-Cl.sub.2Ph     2-FPh 0 H H H H H 111 3,4-Cl.sub.2Ph 2-ClPh 0 H H H H H 112 4-.sub.-t-BuP     h Ph 0 H H H H H 113 4-.sub.-t-BuPh 2-FPh 0 H H H H H 114 4-.sub.-t-BuPh     4-FPh 0 H H H H H 110-113 115 4-.sub.-t-BuPh 2,4-F.sub.2Ph 0 H H H H H     116 4-.sub.-t-BuPh 2-ClPh 0 H H H H H 117 4-.sub.-t-BuPh 4-ClPh 0 H H H     H H (oil).sup.f 118 4-.sub.-t-BuPh 2,4-Cl.sub.2Ph 0 H H H H H 119     2-CH.sub.3 SPh Ph 0 H H H H H 120 2-CH.sub.3 SPh 2-FPh 0 H H H H H 121     2-CH.sub.3 SPh 4-FPh 0 H H H H H 122 2-CH.sub.3 SPh 2,4-F.sub.2Ph 0 H H     H H H 123 2-CH.sub.3 SPh 2-ClPh 0 H H H H H 124 2-CH.sub.3 SPh 4-ClPh 0     H H H H H 125 2-CH.sub.3 SPh 2,4-Cl.sub.2Ph 0 H H H H H 126 2-CH.sub.3     S(O)Ph Ph 0 H H H H H 127 2-CH.sub.3 S(O)Ph 2-FPh 0 H H H H H 128     2-CH.sub.3 S(O)Ph 4-FPh 0 H H H H H 129 2-CH.sub.3 S(O)Ph 2,4-F.sub.2Ph     0 H H H H H 130 2-CH.sub.3 S(O)Ph 2-ClPh 0 H H H H H 131 2-CH.sub.3     S(O)Ph 4-ClPh 0 H H H H H 132 2-CH.sub.3 S(O)Ph 2,4-Cl.sub.2Ph 0 H H H H     H 133 2-CH.sub.3 S(O).sub.2Ph Ph 0 H H H H H 134 2-CH.sub.3 S(O).sub.2Ph     2-FPh 0 H H H H H 135 2-CH.sub.3 S(O).sub.2Ph 4-FPh 0 H H H H H 136     2-CH.sub.3 S(O).sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 137 2-CH.sub.3     S(O).sub.2Ph 2-ClPh 0 H H H H H 138 2-CH.sub.3 S(O).sub.2Ph 4-ClPh 0 H H     H H H 139 2-CH.sub.3 S(O).sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 140     3-CH.sub.3 SPh Ph 0 H H H H H 141 3-CH.sub.3 SPh 2-FPh 0 H H H H H 142     3-CH.sub.3 SPh 4-FPh 0 H H H H H 143 3-CH.sub.3 SPh 2,4-F.sub.2 Ph 0 H H     H H H 144 3-CH.sub.3 SPh 2-ClPh 0 H H H H H 145 3-CH.sub.3 SPh 4-ClPh 0     H H H H H 146 3-CH.sub.3 SPh 2,4-Cl.sub.2Ph 0 H H H H H 147 3-CH.sub.3     S(O)Ph Ph 0 H H H H H 148 3-CH.sub.3 S(O)Ph 2-FPh 0 H H H H H 149     3-CH.sub.3 S(O)Ph 4-FPh 0 H H H H H 150 3-CH.sub.3 S(O)Ph 2,4-F.sub.2Ph     0 H H H H H 151 3-CH.sub.3 S(O)Ph 2-ClPh 0 H H H H H 152 3-CH.sub.3     S(O)Ph 4-ClPh 0 H H H H H 153 3-CH.sub.3 S(O)Ph 2,4-Cl.sub.2Ph 0 H H H H     H 154 3-CH.sub.3 S(O).sub.2Ph Ph 0 H H H H H 155 3-CH.sub.3 S(O).sub.2Ph     2-FPh 0 H H H H H 156 3-CH.sub.3 S(O).sub.2Ph 4-FPh 0 H H H H H 157     3-CH.sub.3 S(O).sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 158 3-CH.sub.3     S(O).sub.2 Ph 2-ClPh 0 H H H H H 159 3-CH.sub.3 S(O).sub.2Ph 4-ClPh 0 H     H H H H 160 3-CH.sub.3 S(O).sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 161     4-CH.sub.3 SPh Ph 0 H H H H H 162 4-CH.sub.3 SPh 2-FPh 0 H H H H H 163     4-CH.sub.3 SPh 4-FPh 0 H H H H H 140-142 164 4-CH.sub.3      SPh 2,4-F.sub.2Ph 0 H H H H H 81-83 165 4-CH.sub.3 SPh 2-ClPh 0 H H H H     H 166 4-CH.sub.3 SPh 4-ClPh 0 H H H H H 167 4-CH.sub.3      SPh 2,4-Cl.sub.2Ph 0 H H H H H 168 4-CH.sub.3 S(O)Ph Ph 0 H H H H H 169     4-CH.sub.3 S(O)Ph 2-FPh 0 H H H H H 170 4-CH.sub.3 S(O)Ph 4-FPh 0 H H H     H H 81-84 171 4-CH.sub.3 S(O)Ph 2,4-F.sub.2Ph 0 H H H H H 131-134 172     4-CH.sub.3 S(O)Ph 2-ClPh 0 H H H H H 173 4-CH.sub.3 S(O)Ph 4-ClPh 0 H H     H H H 174 4-CH.sub.3 S(O)Ph 2,4-Cl.sub.2Ph 0 H H H H H 175 4-CH.sub.3     S(O)Ph Ph 0 H H H H H 176 4-CH.sub.3 S(O).sub.2Ph 2-FPh 0 H H H H H 177     4-CH.sub.3 S(O).sub.2Ph 4-FPh 0 H H H H H 135 178 4-CH.sub.3      S(O).sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 179 4-CH.sub.3 S(O).sub.2Ph     2-ClPh 0 H H H H H 180 4-CH.sub.3 S(O).sub.2Ph 4-ClPh 0 H H H H H 181     4-CH.sub.3 S(O).sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 182 3--n-BuS(O)Ph     4-FPh 0 H H H H H 183 3--n-BuS(O)Ph 2,4-F.sub.2Ph 0 H H H H H 184     3--n-BuS(O)Ph 4-ClPh 0 H H H H H 185 3--n-BuS(O)Ph 2-4-Cl.sub.2Ph 0 H H     H H H 186 2-CF.sub.3 OPh Ph 0 H H H H H 187 2-CF.sub.3 OPh 2-FPh 0 H H H     H H 188 2-CF.sub.3 OPh 4-FPh 0 H H H H H 189 2-CF.sub.3      OPh 2,4-F.sub.2Ph 0 H H H H H 190 2-CF.sub.3 OPh 2-ClPh 0 H H H H H 191     2-CF.sub.3 OPh 4-ClPh 0 H H H H H 192 2-CF.sub.3 OPh 2,4-Cl.sub.2Ph 0 H     H H H H 193 3-CF.sub.3 OPh Ph 0 H H H H H 194 3-CF.sub.3 OPh 2-FPh 0 H H     H H H 195 3-CF.sub.3 OPh 4-FPh 0 H H H H H 196 3-CF.sub.3                P      OPh 2,4-F.sub.2h 0 H H H H H 197 3-CF.sub.3 OPh 2-ClPh 0 H H H H H 198     3-CF.sub.3 OPh 4-ClPh 0 H H H H H 199 3-CF.sub.3 OPh 2,4-Cl.sub.2Ph 0 H     H H H H 200 4-CF.sub.3 OPh Ph 0 H H H H H 201 4-CF.sub.3 OPh 2-FPh 0 H H     H H H 202 4-CF.sub.3 OPh 4-FPh 0 H H H H H 203 4-CF.sub.3                P      OPh 2,4-F.sub.2h 0 H H H H H 204 4-CF.sub.3 OPh 2-ClPh 0 H H H H H 205     4-CF.sub.3 OPh 4-ClPh 0 H H H H H 206 4-CF.sub.3 OPh 2,4-Cl.sub.2Ph 0 H     H H H H 207 4-F-1-naphthyl 2-FPh 0 H H H H H 208 1-naphthyl 4-FPh 0 H H     H H H 104-106 209 1-naphthyl 2,4-F.sub.2Ph 0 H H H H H 210 1-naphthyl     2-ClPh 0 H H H H H 211 2-Cl-1-naphthyl 4-ClPh 0 H H H H H 212 1-naphthyl     2,4-Cl.sub.2Ph 0 H H H H H 213 2-naphthyl 2-FPh 0 H H H H H 214 2-naphthy     l 4-FPh 0 H H H H H 215 2-naphthyl 2,4-F.sub.2Ph 0 H H H H H 216     2-naphthyl 2-Cl 0 H H H H H 217 1-Cl-2-naphthyl 4-ClPh 0 H H H H H 218     2-naphthyl 2,4-Cl.sub.2Ph 0 H H H H H 219 2-thienyl Ph 0 H H H H H 220     2-thienyl 2-FPh 0 H H H H H 221 2-thienyl 4-FPh 0 H H H H H 222 2-thienyl      2,4-F.sub.2Ph 0 H H H H H 223 2-thienyl 2-ClPh 0 H H H H H 224 2-thienyl      4-ClPh 0 H H H H H 225 2-thienyl 2,4-Cl.sub.2Ph 0 H H H H H 226     3-thienyl Ph 0 H H H H H 227 3-thienyl 2-FPh 0 H H H H H 228 3-thienyl     4-FPh 0 H H H H H 229 3-thienyl 2,4-F.sub.2Ph 0 H H H H H 230 3-thienyl     2-ClPh 0 H H H H H 231 3-thienyl 4-ClPh 0 H H H H H 232 3-thienyl     2,4-Cl.sub.2Ph 0 H H H H H 233 2-Cl-3-thienyl Ph 0 H H H H H 234     2-Cl-3-thienyl 2-FPh 0 H H H H H 235 2-Cl-3-thienyl 2-ClPh 0 H H H H H     236 5-Cl-2-thienyl Ph 0 H H H H H 237 5-Cl-2-thienyl 2-FPh 0 H H H H H     238 5-Cl-2-thienyl 2-ClPh 0 H H H H H 239 2,5-Cl.sub.2 -3-thienyl Ph 0 H     H H H H 240 2,5-Cl.sub.2 -3-thienyl 2-FPh 0 H H H H H 241 2,5-Cl.sub.2     -3-thienyl 4-FPh 0 H H H H H 242 2,5-Cl.sub.2 -3-thienyl 2,4-F.sub.2Ph 0     H H H H H 243 2,5-Cl.sub.2      -3-thienyl 2-ClPh 0 H H H H H 244 2,5-Cl.sub.2 -3-thienyl 4-ClPh 0 H H     H H H 245 2,5-Cl.sub.2 -3-thienyl 2,4-Cl.sub.2Ph 0 H H H H H 246     5-bromo-2-thienyl Ph 0 H H H H H 247 5-bromo-2-thienyl 2-FPh 0 H H H H H     248 5-bromo-2-thienyl 4-FPh 0 H H H H H 249 5-bromo-2-thienyl 2,4-F.sub.2P     h 0 H H H H H 250 5-bromo-2-thienyl 2-ClPh 0 H H H H H 251 5-bromo-2-thie     nyl 4-ClPh 0 H H H H H 252 5-bromo-2-thienyl 2,4-Cl.sub.2Ph 0 H H H H H     253 2-pyridyl Ph 0 H H H H H 254 2-pyridyl 2-FPh 0 H H H H H 255     2-pyridyl 2-ClPh 0 H H H H H 256 3-pyridyl Ph 0 H H H H H 257 3-pyridyl     2-FPh 0 H H H H H 258 3-pyridyl 2-ClPh 0 H H H H H 259 4-pyridyl Ph 0 H     H H H H 260 4-pyridyl 2-FPh 0 H H H H H 261 4-pyridyl 2-ClPh 0 H H H H H     262 5-Cl-2-pyridyl Ph 0 H H H H H 263 5-Cl-2-pyridyl 2-FPh 0 H H H H H     264 5-Cl-2-pyridyl 2-ClPh 0 H H H H H 265 2-Cl-3-pyridyl Ph 0 H H H H H     266 2-Cl-3-pyridyl 2-FPh 0 H H H H H 267 2-Cl-3-pyridyl 4-FPh 0 H H H H     H 268 2-Cl-3-pyridyl 2,4-F.sub.2Ph 0 H H H H H 142-143 269 2-Cl-3-pyridyl      2-ClPh 0 H H H H H 270 2-Cl-3-pyridyl 4-ClPh 0 H H H H H 140-145 271     2-Cl-3-pyridyl 2,4-Cl.sub.2Ph 0 H H H H H 272 3-Cl-2-pyridyl Ph 0 H H H     H H 273 3-Cl-2-pyridyl 2-FPh 0 H H H H H 274 3-Cl-2-pyridyl 4-FPh 0 H H     H H H 275 3-Cl-2-pyridyl 2,4-F.sub.2Ph 0 H H H H H 276 3-Cl-2-pyridyl     2-ClPh 0 H H H H H 277 3-Cl-2-pyridyl 4-ClPh 0 H H H H H 278 3-Cl-2-pyrid     yl 2,4-Cl.sub.2Ph 0 H H H H H 279 6-Cl-3-pyridyl Ph 0 H H H H H 280     6-Cl-3-pyridyl 2-FPh 0 H H H H H 281 6-Cl-3-pyridyl 4-FPh 0 H H H H H     282 6-Cl-3-pyridyl 2,4-F.sub.2Ph 0 H H H H H 283 6-Cl-3-pyridyl 2-ClPh 0     H H H H H 284 6-Cl-3-pyridyl 4-ClPh 0 H H H H H 285 6-Cl-3-pyridyl     2,4-Cl.sub.2Ph 0 H H H H H 286 Ph 4-FPh 0 H CH.sub.3 H H H 108-111 287     Ph 4-FPh 0 H F H H H 288 Ph 4-FPh 0 H Cl H H H 289 Ph 4-FPh 0 H Br H H H 2     90 Ph 4-FPh 0 (CH.sub.2).sub.2 H H H 291 Ph 4-FPh 0 H Ph H H H (oil).sup.     g 292 Ph 4-FPh 0 CH.sub.3 CH.sub.3 H H H 293 Ph 4-FPh 0 F F H H H 294 Ph     4-FPh 0 Cl Cl H H H 295 4-FPh 4-FPh 0 H CH.sub.3 H H H 296 4-FPh 4-FPh 0     H F H H H 297 4-FPh 4-FPh 0 H Cl H H H 298 4-FPh 4-FPh 0 H Br H H H 299     4-FPh 4-FPh 0 (CH.sub.2).sub.2 H H H 300 4-FPh 4-FPh 0 CH.sub.3 CH.sub.3 H      H H 301 4-FPh 4-FPh 0 F F H H H 302 4-FPh 4-FPh 0 Cl Cl H H H 303     4-ClPh 2,4-Cl.sub.2Ph 0 H CH.sub.3 H H H 304 4-ClPh 2,4-Cl.sub.2Ph 0 H F     H H H 305 4-ClPh 2,4-Cl.sub.2Ph 0 H Cl H H H 306 4-ClPh 2,4-Cl.sub.2Ph 0     H Br H H H 307 4-ClPh 2,4-Cl.sub.2Ph 0 (CH.sub.2).sub.2 H H H 308 4-ClPh 2     ,4-Cl.sub.2Ph 0 CH.sub.3  CH.sub.3 H H H 309 4-ClPh 2,4-Cl.sub.2Ph 0 F F     H H H 310 4-ClPh 2,4-Cl.sub.2Ph 0 Cl Cl H H H 311 2-ClPh 4-ClPh 0 H     CH.sub.3 H H H 312 2-ClPh 4-ClPh 0 H F H H H 313 2-ClPh 4-ClPh 0 H Cl H     H H 314 2-ClPh 4-ClPh 0 H Br H H H 315 2-ClPh 4-ClPh 0 (CH.sub.2).sub.2     H H H 316 2-ClPh 4-ClPh 0 CH.sub.3 CH.sub.3 H H H 317 2-ClPh 4-ClPh 0 F     F H H H 318 2-ClPh 4-ClPh 0 Cl Cl H H H 319 4-FPh 4-FPh 0 H C.sub.2     H.sub.5 H H H 320 4-FPh 4-FPh 0 H .sub.-i-C.sub.3 H.sub.7 H H H 321     4-FPh 4-FPh 0 H -n-C.sub.4 H.sub.9 H H H 322 4-FPh 4-FPh 0 H Ph H H H     323 4-FPh 4-FPh 0 CH.sub.3 .sub.-t-C.sub.4 H.sub.9 H H H 324 4-FPh 4-FPh     0 CH.sub.3 Ph H H H 325 4-FPh 4-FPh 0 H I H H H 326 4-FPh 4-FPh 0     CH.sub.3 F H H H 327 4-FPh 4-FPh 0 CH.sub.3 Cl H H H 328 4-FPh 4-FPh 0     Br Br H H H 329 4-FPh 4-FPh 0 (CH.sub.2).sub.3 H H H 330 4-FPh 4-FPh 0     (CH.sub.2).sub.4 H H H 331 4-FPh 4-FPh 0 (CH.sub.2).sub.5 H H H 332     4-FPh 4-FPh 0 (CH.sub.2).sub.6 H H H 333 4-CH.sub.3Ph 4-FPh 0 H CH.sub.3 H      H H 334 4-FPh 4-FPh 1 H CH.sub.3 H H H 335 4-ClPh 4-FPh 4 H CH.sub.3 H     H H 336  -n-C.sub.4      F.sub.9 4-FPh 0 H CH.sub.3 H H H 337 (CH.sub.3).sub.2 N 4-FPh 1 H     CH.sub.3 H H H 338 5-Cl-thio- 4-FPh 0 H CH.sub.3 H H H  phen-2-yl 339     2-Cl-thio- 4-FPh 0 H CH.sub.3 H H H  phen-3-yl 340 1-imida- 4-FPh 0 H     CH.sub.3 H H H  soyl 341 1,2,4-tria- 4-FPh 0 H CH.sub.3 H H H  sol-1-yl     342 5-chloro-2- 4-FPh 0 H CH.sub.3 H H H  pyridyl 343 4-FPh -n-C.sub.4     H.sub.9 0 H CH.sub.3 H H H 344 4-FPh .sub.-t-C.sub.4 H.sub.9 0 H     CH.sub.3 H H H 345 4-FPh -n-C.sub.4 H.sub.9 0 H CH.sub.3 H H H 346     4-CH.sub.3Ph 4-FPh 0 H F H H H 347 4-FPh 4-FPh 1 H F H H H 348 4-ClPh    P     4-Fh 4 H F H H H 349 -n-C.sub.4      F.sub.9 4-FPh 0 H F H H H 350 (CH.sub.3).sub.2 N 4-FPh 1 H F H H H 351     5-Cl- 4-FPh 0 H F H H H  thiophen-  2-yl 352 2-Cl- 4-FPh 0 H F H H H     thiophen-  2-yl 353 1-imida- 4-FPh 0 H F H H H  soyl 354 1,2,4- 4-FPh 0     H F H H H  triazol-  1-yl 355 5-Cl-2- 4-FPh 0 H F H H H  pyridyl 356     4-FPh -n-C.sub.4 H.sub.9 0 H F H H H 357 4-FPh .sub.-t-C.sub.4 H.sub.9 0     H F H H H 358 4-FPh -n-C.sub.4     ##STR32##

EXAMPLES 1276 AND 1276 a: Preparation of the (S)-enantiomer of Example49

The compound of Example 49 (1.5 g) and 1.5 g of l-α-bromocamphor-π-sulfonic acid was dissolved in 75 ml of acetonitrile andrefluxed for 2 hours. The solution was allowed to cool to ambienttemperature and stand for 14 hours. Filtration of the resulting solidsfollowed by recrystallization from an additional portion ofacetonitrile, yielded 1.28 g of white solid, mp 216°-217°; [α]_(D) ²⁵=-104° (C=1; DMSO).

The acetonitrile can be evaporated to yield the adduct having a(+)-rotation (Example 1276a). This compound can be recrystallized froman ether/acetone mixture to yield a solid, that on treatment withaqueous NaHCO₃ yields material identical by NMR to that of Example 49.

The solid was suspended in 50 ml of saturated NaHCO₃ solution andstirred vigorously until the evolution of gas ceased (1-2 hours). Themixture was extracted twice with 50 ml of CHCl₃. The organic layers werecombined, washed with brine, dried over Na₂ SO₄ and the solvent removedin vacuo. This yielded 750 mg of a white solid (Example 1276) having an'H NMR identical to that of the compound of Example 49, mp=82°-83°;[α]_(D) ²⁵ =-82° (C=1; CHCl₃).

These compounds and other compounds which were resolved as describedabove are shown in Table 2.

                                      TABLE 2                                     __________________________________________________________________________     ##STR33##                                                                    Ex.                                                                           No.   A        B        n R R.sup.1                                                                         R.sup.2                                                                         R.sup.3                                                                         R.sup.4                                                                         M.P. °C.                                                                    [α].sub.D.sup.25               __________________________________________________________________________    1276                                                                                 ##STR34##                                                                              ##STR35##                                                                             0 H H H H H 82-83                                                                              -62°                          1276a.sup.(1)                                                                        ##STR36##                                                                              ##STR37##                                                                             0 H H H H H 83-84                                                                              +60°                          1277.sup.(2)                                                                         ##STR38##                                                                              ##STR39##                                                                             0 H H H H H 60-61 (HCl salt 181-184)                                                           -67°                          1277a.sup.(1),(2)                                                                    ##STR40##                                                                              ##STR41##                                                                             0 H H H H H 60-62                                                                              +66°                          __________________________________________________________________________     *denotes chiral center                                                        .sup.(1) substitute dα-bromocamphor-π-sulfonic acid                  .sup.(2) use a 3 parts ether  1 part acetone mixture as solvent.         

EXAMPLE 1278 Preparation of2-(4-fluorophenyl)-3-phenyl-1-(5-mercapto-1H-1,2,4-triazol-1-yl)-3-buten-1-ol

To a solution of 1.24 g (0.004 mol) of2-(4-fluorophenyl)-3-phenyl-1-(1H-1,2,4-triazool-1-yl)-3-buten-2-ol in15 mL of THF at -70° was added 5.2 mL (0.008 mol) of a 1.55M solution ofn-butyllithium in hexanes over 5 minutes. After 30 minutes, 0.13 g(0.004 mol) of sulfur was added and the reaction mixture was allowed towarm to room temperature over 1 h, then quenched with 8 mL of 1N HCl.After pouring into saturated NH₄ Cl, the mixture was extracted with 2×ether and the combined organic layers were washed with brine, dried overNa₂ SO₄ and evaporated. The crude product was purified by flashchromatography using 2:13:85 methanol/ether/methylene chloride to give0.85 g of the title compound, m.p. 54°-58°; NMR (CDCl₃) δ 4.7 (ABq, 2H),5.0 (s, 1H, OH) 5.3 (s, 1H, vinyl), 5.5 (s, 1H, vinyl), 7.0 (m, 4H), 7.2(m, 3H), 7.5 (m, 2H), 7.7 (s, 1H, triazole proton), 12.5 (brs, 1H, SH);IR (methylene chloride) 3500-3000 (br), 1590, 1500, 1465, 1230, 1162,1109, 825 cm⁻¹ ; MS: highest m/e 341.

The compounds shown in Table 3 were prepared or can be prepared by themethods described above.

                                      TABLE 3*                                    __________________________________________________________________________     ##STR42##                                                                    Ex.                                                                           No. A      B      R R.sup.1                                                                         R.sup.2                                                                         R.sup.4                                                                         Q             M.P.°C.                        __________________________________________________________________________    1278                                                                              Ph     4-FPh  H H H H SH            54-58                                 1279                                                                              Ph     Ph     H H H H SH                                                  1280                                                                              Ph     2-FPh  H H H H SH                                                  1281                                                                              Ph     2-ClPh H H H H SH                                                  1282                                                                              Ph     4-ClPh H H H H SH                                                  1283                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H SH                                                  1284                                                                              Ph     2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1285                                                                              2-FPh  Ph     H H H H SH                                                  1286                                                                              2-FPh  2-FPh  H H H H SH                                                  1287                                                                              2-FPh  4-FPh  H H H H SH                                                  1288                                                                              2-FPh  2-ClPh H H H H SH                                                  1289                                                                              2-FPh  4-ClPh H H H H SH                                                  1290                                                                              2-FPh  2,4-F.sub.2Ph                                                                        H H H H SH                                                  1291                                                                              2-FPh  2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1292                                                                              3-FPh  Ph     H H H H SH                                                  1293                                                                              3-FPh  2-FPh  H H H H SH                                                  1294                                                                              3-FPh  4-FPh  H H H H SH                                                  1295                                                                              3-FPh  2-ClPh H H H H SH                                                  1296                                                                              3-FPh  4-ClPh H H H H SH                                                  1297                                                                              3-FPh  2,4-F.sub.2Ph                                                                        H H H H SH                                                  1298                                                                              3-FPh  2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1299                                                                              4-FPh  Ph     H H H H SH                                                  1300                                                                              4-FPh  2-FPh  H H H H SH            144.5-148                             1301                                                                              4-FPh  4-FPh  H H H H SH                                                  1302                                                                              4-FPh  2-ClPh H H H H SH                                                  1303                                                                              4-FPh  4-ClPh H H H H SH                                                  1304                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H SH            (foam).sup.a                          1305                                                                              4-FPh  2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1306                                                                              2-ClPh Ph     H H H H SH                                                  1307                                                                              2-Cl Ph                                                                              2-FPh  H H H H SH                                                  1308                                                                              2-ClPh 4-FPh  H H H H SH                                                  1309                                                                              2-ClPh 2-ClPh H H H H SH                                                  1310                                                                              2-ClPh 4-ClPh H H H H SH                                                  1311                                                                              2-ClPh 2,4-F.sub.2Ph                                                                        H H H H SH                                                  1312                                                                              2-ClPh 2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1313                                                                              3-ClPh Ph     H H H H SH                                                  1314                                                                              3-ClPh 2-FPh  H H H H SH                                                  1315                                                                              3-ClPh 4-FPh  H H H H SH                                                  1316                                                                              3-ClPh 2-ClPh H H H H SH                                                  1317                                                                              3-ClPh 4-ClPh H H H H SH                                                  1318                                                                              3-ClPh 2,4-F.sub.2Ph                                                                        H H H H SH                                                  1319                                                                              3-ClPh 2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1320                                                                              4-ClPh Ph     H H H H SH                                                  1321                                                                              4-ClPh 2-FPh  H H H H SH                                                  1322                                                                              4-ClPh 4-FPh  H H H H SH                                                  1323                                                                              4-ClPh 2-ClPh H H H H SH                                                  1324                                                                              4-ClPh 4-ClPh H H H H SH                                                  1325                                                                              4-ClPh 2,4-F.sub.2Ph                                                                        H H H H SH                                                  1326                                                                              4-ClPh 2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1327                                                                              2-CF.sub.3Ph                                                                         Ph     H H H H SH                                                  1328                                                                              2-CF.sub.3Ph                                                                         2-FPh  H H H H SH                                                  1329                                                                              2-CF.sub.3Ph                                                                         4-FPh  H H H H SH                                                  1330                                                                              2-CF.sub.3Ph                                                                         2-ClPh H H H H SH                                                  1331                                                                              2-CF.sub.3Ph                                                                         4-ClPh H H H H SH                                                  1332                                                                              2-CF.sub.3Ph                                                                         2,4-F.sub.2Ph                                                                        H H H H SH                                                  1333                                                                              2-CF.sub.3Ph                                                                         2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1334                                                                              4-CF.sub.3Ph                                                                         Ph     H H H H SH                                                  1335                                                                              4-CF.sub.3Ph                                                                         2-FPh  H H H H SH                                                  1336                                                                              4-CF.sub.3Ph                                                                         4-FPh  H H H H SH                                                  1337                                                                              4-CF.sub.3Ph                                                                         2-ClPh H H H H SH                                                  1338                                                                              4-CF.sub.3Ph                                                                         4-ClPh H H H H SH                                                  1339                                                                              4-CF.sub.3Ph                                                                         2,4-F.sub.2Ph                                                                        H H H H SH                                                  1340                                                                              4-CF.sub.3Ph                                                                         2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1341                                                                              2,4-F.sub.2Ph                                                                        Ph     H H H H SH                                                  1342                                                                              2,4-F.sub.2Ph                                                                        2-FPh  H H H H SH                                                  1343                                                                              2,4-F.sub.2Ph                                                                        4-FPh  H H H H SH                                                  1344                                                                              2,4-F.sub.2Ph                                                                        2-ClPh H H H H SH                                                  1345                                                                              2,4-F.sub.2Ph                                                                        4-ClPh H H H H SH                                                  1346                                                                              2,4-F.sub.2Ph                                                                        2,4-F.sub.2Ph                                                                        H H H H SH                                                  1347                                                                              2,4-F.sub.2Ph                                                                        2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1348                                                                              2,4-Cl.sub.2Ph                                                                       Ph     H H H H SH                                                  1349                                                                              2,4-Cl.sub.2Ph                                                                       2-FPh  H H H H SH                                                  1350                                                                              2,4-Cl.sub.2Ph                                                                       4-FPh  H H H H SH                                                  1351                                                                              2,4-Cl.sub.2Ph                                                                       2-ClPh H H H H SH                                                  1352                                                                              2,4-Cl.sub.2Ph                                                                       4-ClPh H H H H SH                                                  1353                                                                              2,4-Cl.sub.2Ph                                                                       2,4-F.sub.2Ph                                                                        H H H H SH                                                  1354                                                                              2,4-Cl.sub.2Ph                                                                       2,4-Cl.sub.2Ph                                                                       H H H H SH                                                  1355                                                                              Ph     Ph     H H H H I                                                   1356                                                                              Ph     2-FPh  H H H H I                                                   1357                                                                              Ph     4-FPh  H H H H I                                                   1358                                                                              Ph     2-ClPh H H H H I                                                   1359                                                                              Ph     4-ClPh H H H H I                                                   1360                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H I                                                   1361                                                                              Ph     2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1362                                                                              2-FPh  Ph     H H H H I                                                   1363                                                                              2-FPh  2-FPh  H H H H I                                                   1364                                                                              2-FPh  4-FPh  H H H H I                                                   1365                                                                              2-FPh  2-ClPh H H H H I                                                   1366                                                                              2-FPh  4-ClPh H H H H I                                                   1367                                                                              2-FPh  2,4-F.sub.2Ph                                                                        H H H H I                                                   1368                                                                              2-FPh  2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1369                                                                              3-FPh  Ph     H H H H I                                                   1370                                                                              3-FPh  2-FPh  H H H H I                                                   1371                                                                              3-FPh  4-FPh  H H H H I                                                   1372                                                                              3-FPh  2-ClPh H H H H I                                                   1373                                                                              3-FPh  4-ClPh H H H H I                                                   1374                                                                              3-FPh  2,4-F.sub.2Ph                                                                        H H H H I                                                   1375                                                                              3-FPh  2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1376                                                                              4-FPh  Ph     H H H H I                                                   1377                                                                              4-FPh  2-FPh  H H H H I             96-97.5                               1378                                                                              4-FPh  4-FPh  H H H H I                                                   1379                                                                              4-FPh  2-ClPh H H H H I                                                   1380                                                                              4-FPh  4-ClPh H H H H I                                                   1381                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H I             (foam).sup.b                          1382                                                                              4-FPh  2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1383                                                                              2-ClPh Ph     H H H H I                                                   1384                                                                              2-ClPh 2-FPh  H H H H I                                                   1385                                                                              2-ClPh 4-FPh  H H H H I                                                   1386                                                                              2-ClPh 2-ClPh H H H H I                                                   1387                                                                              2-ClPh 4-ClPh H H H H I                                                   1388                                                                              2-ClPh 2,4-F.sub.2Ph                                                                        H H H H I                                                   1389                                                                              2-ClPh 2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1390                                                                              3-ClPh Ph     H H H H I                                                   1391                                                                              3-ClPh 2-FPh  H H H H I                                                   1392                                                                              3-ClPh 4-FPh  H H H H I                                                   1393                                                                              3-ClPh 2-ClPh H H H H I                                                   1394                                                                              3-ClPh 4-ClPh H H H H I                                                   1395                                                                              3-ClPh 2,4-F.sub.2Ph                                                                        H H H H I                                                   1396                                                                              3-ClPh 2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1397                                                                              4-ClPh Ph     H H H H I                                                   1398                                                                              4-ClPh 2-FPh  H H H H I                                                   1399                                                                              4-ClPh 4-FPh  H H H H I                                                   1400                                                                              4-ClPh 2-ClPh H H H H I                                                   1401                                                                              4-ClPh 4-ClPh H H H H I                                                   1402                                                                              4-ClPh 2,4-F.sub.2Ph                                                                        H H H H I                                                   1403                                                                              4-ClPh 2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1404                                                                              2-CF.sub.3Ph                                                                         Ph     H H H H I                                                   1405                                                                              2-CF.sub.3Ph                                                                         2-FPh  H H H H I                                                   1406                                                                              2-CF.sub.3Ph                                                                         4-FPh  H H H H I                                                   1407                                                                              2-CF.sub.3Ph                                                                         2-ClPh H H H H I                                                   1408                                                                              2-CF.sub.3Ph                                                                         4-ClPh H H H H I                                                   1409                                                                              2-CF.sub.3Ph                                                                         2,4-F.sub.2Ph                                                                        H H H H I                                                   1410                                                                              2-CF.sub.3Ph                                                                         2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1411                                                                              4-CF.sub.3Ph                                                                         Ph     H H H H I                                                   1412                                                                              4-CF.sub.3Ph                                                                         2-FPh  H H H H I                                                   1413                                                                              4-CF.sub.3Ph                                                                         4-FPh  H H H H I                                                   1414                                                                              4-CF.sub.3Ph                                                                         2-ClPh H H H H I                                                   1415                                                                              4-CF.sub.3Ph                                                                         4-ClPh H H H H I                                                   1416                                                                              4-CF.sub.3Ph                                                                         2,4-F.sub.2Ph                                                                        H H H H I                                                   1417                                                                              4-CF.sub.3Ph                                                                         2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1418                                                                              2,4-F.sub.2Ph                                                                        Ph     H H H H I                                                   1419                                                                              2,4-F.sub.2Ph                                                                        2-FPh  H H H H I                                                   1420                                                                              2,4-F.sub.2Ph                                                                        4-FPh  H H H H I                                                   1421                                                                              2,4-F.sub.2Ph                                                                        2-ClPh H H H H I                                                   1422                                                                              2,4-F.sub.2Ph                                                                        4-ClPh H H H H I                                                   1423                                                                              2,4-F.sub.2Ph                                                                        2,4-F.sub.2Ph                                                                        H H H H I                                                   1424                                                                              2,4-F.sub.2Ph                                                                        2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1425                                                                              2,4-Cl.sub.2Ph                                                                       Ph     H H H H I                                                   1426                                                                              2,4-Cl.sub.2Ph                                                                       2-FPh  H H H H I                                                   1427                                                                              2,4-Cl.sub.2Ph                                                                       4-FPh  H H H H I                                                   1428                                                                              2,4-Cl.sub.2Ph                                                                       2-ClPh H H H H I                                                   1429                                                                              2,4-Cl.sub.2Ph                                                                       4-ClPh H H H H I                                                   1430                                                                              2,4-Cl.sub.2Ph                                                                       2,4-F.sub.2Ph                                                                        H H H H I                                                   1431                                                                              2,4-Cl.sub.2Ph                                                                       2,4-Cl.sub.2Ph                                                                       H H H H I                                                   1432                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H SS                                                  1433                                                                              4-FPh  2-FPh  H H H H SS                                                  1434                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H SS                                                  1435                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H SSCH.sub.3                                          1436                                                                              4-FPh  2-FPh  H H H H SSCH.sub.3                                          1437                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H SSCH.sub.3                                          1438                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H                                                                                ##STR43##                                          1439                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR44##                                          1440                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H                                                                                ##STR45##                                          1441                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H                                                                                ##STR46##                                          1442                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR47##                                          1443                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H                                                                                ##STR48##                                          1444                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H Cl                                                  1445                                                                              4-FPh  2-FPh  H H H H Cl                                                  1446                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H Cl                                                  1447                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H CHO                                                 1448                                                                              4-FPh  2-FPh  H H H H CHO                                                 1449                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H CHO                                                 1450                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H SCH.sub.2 CN                                        1451                                                                              4-FPh  2-FPh  H H H H SCH.sub.2 CN  oil.sup.c                             1452                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H SCH.sub.2 CN                                        1453                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H SCH.sub.2 SCN                                       1454                                                                              4-FPh  2-FPh  H H H H SCH.sub.2 SCN                                       1455                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H SCH.sub.2 SCN                                       1456                                                                              Ph     2,4-F.sub.2Ph                                                                        H H H H SCCl.sub.3                                          1457                                                                              4-FPh  2-FPh  H H H H SCCl.sub.3                                          1458                                                                              4-FPh  2,4-F.sub.2Ph                                                                        H H H H SCCl.sub.3                                          1459                                                                              Ph     4-FPh  H H H H S- -n-Bu      semi-solid.sup.d                      1460                                                                              4-FPh  2-FPh  H H H H F                                                   1461                                                                              4-FPh  2-FPh  H H H H Br                                                  1462                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR49##                                          1463                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR50##                                          1464                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR51##                                          1465                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR52##                                          1466                                                                              4-FPh  2-FPh  H H H H SCF.sub.2 H                                         1467                                                                              4-FPh  2-FPh  H H H H SCF.sub.2 CF.sub.2 H                                1468*                                                                             4-FPh  2-FPh  H H H H                                                                                ##STR53##    (oil).sup.e                           1469*                                                                             4-FPh  2-FPh  H H H H                                                                                ##STR54##    (oil).sup.f                           1470                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR55##                                          1471                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR56##                                          1472                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR57##                                          1473                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR58##                                          1474                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR59##                                          1475                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR60##                                          1476                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR61##                                          1477                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR62##                                          1478                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR63##                                          1479                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR64##                                          1480                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR65##                                          1481                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR66##                                          1482                                                                              4-FPh  2-FPh  H H H H                                                                                ##STR67##                                          1483                                                                              4-FPh  2-FPh  H H H H SCN                                                 1484                                                                              4-FPh  2-FPh  H H H H SSCH.sub.2 Ph                                       1485                                                                              4-FPh  2-FPh  H H H H SS-allyl                                            1486                                                                              4-FPh  2-FPh  H H H H SSPh                                                __________________________________________________________________________     *All compounds in this table are compounds in which E is a bond except        1468 and 1469 in which E is an oxygen atom.                                   .sup.a NMR: (CDCl.sub.3)δ4.9(s, 2H);5.1(s, 1H);5.2(s, 1H);5.3(s,        1H);6.7(m, 2H);6.9(m, 2H);7.2(m, 2H);7.5(m, 1H);7.6(s, 1H);12.2(brs, 1H).     .sup.b NMR: (CDCl.sub.3)δ 4.7(ABq, 2H);5.3(s, 2H);5.8(s, 1H);6.7(m,     2H);6.9(m, 2H);7.3(m, 2H);7.5(m, 1H);7.8(s, 1H).                              .sup.c NMR: (CDCl.sub.3)δ3.8(ABq, 2H);4.7(ABq, 2H);5.2(s,               1H);5.3(two s, 2H);6.9-7.2(m, 4H);7.2-7.4(m, 3H);7.5(m, 1H);7.8(s, 1H).       .sup.d NMR: (CDCl.sub.3)δ0.92(t, 3H);1.4-1.7(m, 4H);3.1(t,              2H);4.5(ABq, 2H);5.4(two s, 2H);5.8(s, 1H);7.0(m, 4H);7.2(m, 3H);7.5(m,       2H);7.8(s, 1H).                                                               .sup.e NMR: (CDCl.sub.3)δ2.7-3.5(m, 2H);4.3(s, 1H);4.4(m, 2H);5.2(m     2H);6.8-7.4(m, 8H);7.9(m, 1H).                                                .sup.f NMR: (CDCl.sub.3)δ2.7-3.4(m, 2H);4.2(d, 1H);4.5(ABq,             2H);5.3(m, 2H);6.8-7.4(m, 8H);7.9(d, 1H).                                

EXAMPLE 1487 Preparation of 2,3-bis(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3,4-epoxy-2-butanol

2,3-Bis(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-butene-2-ol (1.0 g)was dissolved in 50 ml of anhydrous benzene and stirred under nitrogen.To this solution was added 0.012 g of vanadium acetonyl-acetonate. Thesolution was then refluxed and tert-butyl hydroperoxide (0.44 gdissolved in 5 ml of anhydrous benzene) was added dropwise over 10minutes. The reaction was refluxed for one additional hour and thencooled to ambient temperature. The benzene was removed in vacuo and theresidue chromatographed on silica gel (2% MeOH/CH₂ Cl₂). This yielded atotal of 650 mg of diastereomeric products in a 3:1 ratio. Furtherchromatography resulted in the separation of the diastereomers. Themajor isomer was a waxy white solid. NMR (CDCl₃ /TMS) δ 2.60 (d, J=6 Hz,1H); 3.48 (d, J=6 Hz, 1H); 4.70 (q, J=7 Hz, 2H); 5.25 (s, 1H); 6.8-7.3(m, 8H); 7.55 (s, 1H); 7.90 (s, 1H).

The minor isomer was an amorphous white solid. NMR (CDCl₃ /TMS) δ 2.55(d, J=6H, 1H); 2.75 (d, J=6 Hz, 1H); 4.80, (q, J=7 Hz); 5.0 (s, 1H);6.85-7.10 (m, 4H); 7.15-7.45 (m, 4H); 7.80 (s, 1H); 8.05 (s, 1H).

The epoxides shown in Table 4 were prepared or can be prepared by themethod described in Example 1487.

                                      TABLE 4                                     __________________________________________________________________________     ##STR68##                                                                    Ex.                                                                           No.                                                                              A          B       n R  R.sup.1                                                                           R.sup.2 R.sup.3                                                                          R.sup.4                                                                          M.P. °C.                  __________________________________________________________________________    1487                                                                             4-FPh      4-FPh   0 H  H   H       H  H  53-55                            1488                                                                             4-FPh      2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1489                                                                             4-FPh      4-ClPh  0 H  H   H       H  H                                   1490                                                                             4-FPh      2,4-F.sub.2Ph                                                                         0 H  H   H       H  H  (semi-solid).sup.a               1491                                                                             4-FPh      4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1492                                                                             4-FPh      2-FPh   0 H  H   H       H  H  (110-119)                        1493                                                                             4-FPh      2-ClPh  0 H  H   H       H  H                                   1494                                                                             4-FPh       -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1495                                                                             3-FPh      4-FPh   0 H  H   H       H  H                                   1496                                                                             3-FPh      2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1497                                                                             3-FPh      4-ClPh  0 H  H   H       H  H                                   1498                                                                             3-FPh      2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1499                                                                             3-FPh      4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1500                                                                             3-FPh      2-FPh   0 H  H   H       H  H                                   1501                                                                             3-FPh      2-ClPh  0 H  H   H       H  H                                   1502                                                                             3-FPh       -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1503                                                                             4-ClPh     4-FPh   0 H  H   H       H  H                                   1504                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1505                                                                             4-ClPh     4-ClPh  0 H  H   H       H  H                                   1506                                                                             4-ClPh     2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1507                                                                             4-ClPh     4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1508                                                                             4-ClPh     2-FPh   0 H  H   H       H  H                                   1509                                                                             4-ClPh     2-ClPh  0 H  H   H       H  H                                   1510                                                                             4-ClPh      -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1511                                                                             2-ClPh     4-FPh   0 H  H   H       H  H                                   1512                                                                             2-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1513                                                                             2-ClPh     4-ClPh  0 H  H   H       H  H  149-150 Low R.sub.f isomer                                                    141-143 High R.sub.f isomer      1514                                                                             2-ClPh     2,4-F.sub.2Ph                                                                         0 H  H   H       H  H  138-140 Isomer A                                                              152-156 Isomer B                 1515                                                                             2-ClPh     4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1516                                                                             2-ClPh     2-FPh   0 H  H   H       H  H                                   1517                                                                             2-ClPh     2-ClPh  0 H  H   H       H  H                                   1518                                                                             2-ClPh      -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1519                                                                             3-ClPh     4-FPh   0 H  H   H       H  H                                   1520                                                                             3-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1521                                                                             3-ClPh     4-ClPh  0 H  H   H       H  H                                   1522                                                                             3-ClPh     2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1523                                                                             3-ClPh     4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1524                                                                             3-ClPh     2-FPh   0 H  H   H       H  H                                   1525                                                                             3-ClPh     2-ClPh  0 H  H   H       H  H                                   1526                                                                             3-ClPh      -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1527                                                                             Ph         4-FPh   0 H  H   H       H  H  88-94                            1528                                                                             Ph         2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1529                                                                             Ph         4-ClPh  0 H  H   H       H  H  156-158                          1530                                                                             Ph         2,4-F.sub.2Ph                                                                         0 H  H   H       H  H  87-90 Low R.sub.f isomer                                                      148-150 High R.sub.f isomer      1531                                                                             Ph         4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1532                                                                             Ph         2-FPh   0 H  H   H       H  H                                   1533                                                                             Ph         2-ClPh  0 H  H   H       H  H                                   1534                                                                             Ph          -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1535                                                                             4-CF.sub.3Ph                                                                             4-FPh   0 H  H   H       H  H                                   1536                                                                             4-CF.sub.3Ph                                                                             2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1537                                                                             4-CF.sub.3Ph                                                                             4-ClPh  0 H  H   H       H  H                                   1538                                                                             4-CF.sub.3Ph                                                                             2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1539                                                                             4-CF.sub.3Ph                                                                             4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1540                                                                             4-CF.sub.3Ph                                                                             2-FPh   0 H  H   H       H  H                                   1541                                                                             4-CF.sub.3Ph                                                                             2-ClPh  0 H  H   H       H  H                                   1542                                                                             4-CF.sub.3Ph                                                                              -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1543                                                                             4-BrPh     4-FPh   0 H  H   H       H  H                                   1544                                                                             4-BrPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1545                                                                             4-BrPh     4-ClPh  0 H  H   H       H  H                                   1546                                                                             4-BrPh     2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1547                                                                             4-BrPh     4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1548                                                                             4-BrPh     2-FPh   0 H  H   H       H  H                                   1549                                                                             4-BrPh     2-ClPh  0 H  H   H       H  H                                   1550                                                                             4-BrPh      -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1551                                                                             2,4-Cl.sub.2Ph                                                                           4-FPh   0 H  H   H       H  H                                   1552                                                                             2,4-Cl.sub.2Ph                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1553                                                                             2,4-Cl.sub.2Ph                                                                           4-ClPh  0 H  H   H       H  H                                   1554                                                                             2,4-Cl.sub.2Ph                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1555                                                                             2,4-Cl.sub.2Ph                                                                           4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1556                                                                             2,4-Cl.sub.2Ph                                                                           2-FPh   0 H  H   H       H  H                                   1557                                                                             2,4-Cl.sub.2Ph                                                                           2-ClPh  0 H  H   H       H  H                                   1558                                                                             2,4-Cl.sub.2Ph                                                                            -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1559                                                                             2-FPh      4-FPh   0 H  H   H       H  H                                   1560                                                                             2-FPh      2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1561                                                                             2-FPh      4-ClPh  0 H  H   H       H  H                                   1562                                                                             2-FPh      2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1563                                                                             2-FPh      4-CFPh  0 H  H   H       H  H                                   1564                                                                             2-FPh      2-FPh   0 H  H   H       H  H                                   1565                                                                             2-FPh      2-ClPh  0 H  H   H       H  H                                   1566                                                                             2-FPh       -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1567                                                                             2,4-F.sub.2Ph                                                                            4-FPh   0 H  H   H       H  H                                   1568                                                                             2,4-F.sub.2Ph                                                                            2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1569                                                                             2,4-F.sub.2Ph                                                                            4-ClPh  0 H  H   H       H  H                                   1570                                                                             2,4-F.sub.2Ph                                                                            2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1571                                                                             2,4-F.sub.2Ph                                                                            4-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1572                                                                             2,4-F.sub.2Ph                                                                            2-FPh   0 H  H   H       H  H                                   1573                                                                             2,4-F.sub.2Ph                                                                            2-ClPh  0 H  H   H       H  H                                   1574                                                                             2,4-F.sub.2Ph                                                                             -n-C.sub.4 F.sub.9                                                                   0 H  H   H       H  H                                   1575                                                                             Ph         4-FPh   0 H  CH.sub.3                                                                          H       H  H                                   1576                                                                             Ph         4-FPh   0 (CH.sub.2).sub.2                                                                     H       H  H                                   1577                                                                             Ph         4-FPh   0 CH.sub.3                                                                         CH.sub.3                                                                          H       H  H                                   1578                                                                             4-FPh      4-FPh   0 H  CH.sub.3                                                                          H       H  H                                   1579                                                                             4-FPh      4-FPh   0 (CH.sub.2).sub.2                                                                     H       H  H                                   1580                                                                             4-FPh      4-FPh   0 CH.sub.3                                                                         CH.sub.3                                                                          H       H  H                                   1581                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  CH.sub.3                                                                          H       H  H                                   1582                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 (CH.sub.2).sub.2                                                                     H       H  H                                   1583                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 CH.sub.3                                                                         CH.sub.3                                                                          H       H  H                                   1584                                                                             2-ClPh     4-ClPh  0 H  CH.sub.3                                                                          H       H  H                                   1585                                                                             2-ClPh     4-ClPh  0 (CH.sub.2).sub.2                                                                     H       H  H                                   1586                                                                             2-ClPh     4-ClPh  0 CH.sub.3                                                                         CH.sub.3                                                                          H       H  H                                   1587                                                                             4-FPh      4-FPh   0 H  C.sub.2 H.sub.5                                                                   H       H  H                                   1588                                                                             4-FPh      4-FPh   0 H   .sub.-i-C.sub.3 H.sub.7                                                          H       H  H                                   1589                                                                             4-FPh      4-FPh   0 H   -n-C.sub.4 H.sub.9                                                               H       H  H                                   1590                                                                             4-FPh      4-FPh   0 H  Ph  H       H  H                                   1591                                                                             4-FPh      4-FPh   0 H   .sub.-t-C.sub.4 H.sub.9                                                          H       H  H                                   1592                                                                             4-FPh      4-FPh   0 H  Ph  H       H  H                                   1593                                                                             4-FPh      4-FPh   0 CH.sub.3                                                                          .sub.-t-C.sub.4 H.sub.9                                                          H       H  H                                   1594                                                                             4-F Ph     4-FPh   0 CH.sub.3                                                                         Ph  H       H  H                                   1595                                                                             4-FPh      4-FPh   0 (CH.sub.2).sub.3                                                                     H       H  H                                   1596                                                                             4-FPh      4-FPh   0 (CH.sub.2).sub.4                                                                     H       H  H                                   1597                                                                             4-FPh      4-FPh   0 (CH.sub.2).sub.5                                                                     H       H  H                                   1598                                                                             4-FPh      4-FPh   0 (CH.sub.2).sub.6                                                                     H       H  H                                   1599                                                                             4-CH.sub.3Ph                                                                             4-FPh   0 H  CH.sub.3                                                                          H       H  H                                   1600                                                                             4-FPh      4-FPh   1 H  CH.sub.3                                                                          H       H  H                                   1601                                                                             4-ClPh     4-FPh   4 H  CH.sub.3                                                                          H       H  H                                   1602                                                                              -n-C.sub.4 F.sub.9                                                                      4-FPh   0 H  CH.sub.3                                                                          H       H  H                                   1603                                                                             (CH.sub.3).sub.2 N                                                                       4-FPh   1 H  CH.sub.3                                                                          H       H  H                                   1604                                                                             5-Cl-2-thienyl                                                                           4-FPh   0 H  CH.sub.3                                                                          H       H  H                                   1605                                                                             2-Cl-3-thienyl                                                                           4-FPh   0 H  CH.sub.3                                                                          H       H  H                                   1606                                                                             1-imidazoyl                                                                              4-FPh   0 H  CH.sub.3                                                                          H       H  H                                   1607                                                                             4-FPh      4-FPh   0 H  H   CH.sub.3                                                                              H  H                                   1608                                                                             4-FPh      4-FPh   0 H  H   CH.sub.2 CHCH.sub.2                                                                   H  H                                   1609                                                                             4-FPh      4-FPh   0 H  H   COCH.sub.3                                                                            H  H                                   1610                                                                             4-FPh      4-FPh   0 H  H   CO.sub.2 CH.sub.3                                                                     H  H                                   1611                                                                             4-CF.sub.3 OPh                                                                           4-FPh   0 H  H   H       H  H                                   1612                                                                             2-ClPh     4-ClPh  0 H  H   CH.sub.3                                                                              H  H                                   1613                                                                             2-ClPh     4-ClPh  0 H  H   CH.sub.2 CHCH.sub.2                                                                   H  H                                   1614                                                                             2-ClPh     4-ClPh  0 H  H   COCH.sub.3                                                                            H  H                                   1615                                                                             2-ClPh     4-ClPh  0 H  H   CO.sub.2 CH.sub.3                                                                     H  H                                   1616                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   CH.sub.3                                                                              H  H                                   1617                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   CH.sub.2 CHCH.sub.2                                                                   H  H                                   1618                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   COCH.sub.3                                                                            H  H                                   1619                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   CO.sub.2 CH.sub.3                                                                     H  H                                   1620                                                                             Ph         4-FPh   0 H  H   CH.sub.3                                                                              H  H                                   1621                                                                             Ph         4-FPh   0 H  H   CH.sub.2 CHCH.sub.2                                                                   H  H                                   1622                                                                             Ph         4-FPh   0 H  H   COCH.sub.3                                                                            H  H                                   1623                                                                             Ph         4-FPh   0 H  H   CO.sub.2 CH.sub.3                                                                     H  H                                   1624                                                                             OH         2,4-Cl.sub.2Ph                                                                        2 H  H   H       H  H                                   1625                                                                             OH         2,4-Cl.sub.2Ph                                                                        3 H  H   H       H  H                                   1626                                                                             OH         2,4-Cl.sub.2Ph                                                                        4 H  H   H       H  H                                   1627                                                                             1-imidazoyl                                                                              2,4-Cl.sub.2Ph                                                                        1 H  H   H       H  H                                   1628                                                                             1-imidazoyl                                                                              2,4-Cl.sub.2Ph                                                                        2 H  H   H       H  H                                   1629                                                                             1-imidazoyl                                                                              4-FPh   3 H  H   H       H  H                                   1630                                                                             1-imidazoyl                                                                              4-FPh   4 H  H   H       H  H                                   1631                                                                             1H-1,2,4-triazoyl-1-yl                                                                   4-FPh   1 H  H   H       H  H                                   1632                                                                             1H-1,2,4-triazoyl-1-yl                                                                   4-FPh   2 H  H   H       H  H                                   1633                                                                             1H-1,2,4-triazoyl-1-yl                                                                   4-FPh   3 H  H   H       H  H                                   1634                                                                             1H-1,2,4-triazoyl-1-yl                                                                   4-FPh   4 H  H   H       H  H                                   1635                                                                             1H-1,2,4-triazoyl-1-yl                                                                   2,4-Cl.sub.2Ph                                                                        1 H  H   H       H  H                                   1636                                                                             Ph         2,5-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1637                                                                             Ph         3-FPh   0 H  H   H       H  H                                   1638                                                                             Ph         2,5-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1639                                                                             Ph         3-ClPh  0 H  H   H       H  H                                   1640                                                                             Ph         4-BrPh  0 H  H   H       H  H                                   1641                                                                             Ph         4-IPh   0 H  H   H       H  H                                   1642                                                                             Ph         3,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1643                                                                             Ph         3,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1644                                                                             Ph         2,6-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1645                                                                             Ph         2-Cl-(4-F)Ph                                                                          0 H  H   H       H  H                                   1646                                                                             Ph         2,4,6-Cl.sub.3Ph                                                                      0 H  H   H       H  H                                   1647                                                                             Ph         2-F-(4-Cl)Ph                                                                          0 H  H   H       H  H                                   1648                                                                             Ph         Ph      0 H  H   H       H  H                                   1649                                                                             Ph         4-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1650                                                                             Ph         3-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1651                                                                             Ph         2-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1652                                                                             Ph         2-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1653                                                                             Ph         3-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1654                                                                             Ph         2-F-(4-CF.sub.3)Ph                                                                    0 H  H   H       H  H                                   1655                                                                             Ph         4-CH.sub.3 OPh                                                                        0 H  H   H       H  H                                   1656                                                                             Ph         5-Cl-2-pyridyl                                                                        0 H  H   H       H  H                                   1657                                                                             Ph         5-Cl-2-thienyl                                                                        0 H  H   H       H  H                                   1658                                                                             Ph         2-Cl-3-thienyl                                                                        0 H  H   H       H  H                                   1659                                                                             Ph          .sub.-s-C.sub.4 H.sub.9                                                              0 H  H   H       H  H                                   1660                                                                             2-ClPh     2,5-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1661                                                                             2-ClPh     3-FPh   0 H  H   H       H  H                                   1662                                                                             2-ClPh     2,5-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1663                                                                             2-ClPh     3-ClPh  0 H  H   H       H  H                                   1664                                                                             2-ClPh     4-BrPh  0 H  H   H       H  H                                   1665                                                                             2-ClPh     4-IPh   0 H  H   H       H  H                                   1666                                                                             2-ClPh     3,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1667                                                                             2-ClPh     3,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1668                                                                             2-ClPh     2,6-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1669                                                                             2-ClPh     2-Cl-(4-F)Ph                                                                          0 H  H   H       H  H                                   1670                                                                             2-ClPh     2,4,6-Cl.sub.3Ph                                                                      0 H  H   H       H  H                                   1671                                                                             2-ClPh     2-F-(4-Cl)Ph                                                                          0 H  H   H       H  H                                   1672                                                                             2-ClPh     Ph      0 H  H   H       H  H                                   1673                                                                             2-ClPh     4-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1674                                                                             2-ClPh     3-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1675                                                                             2-ClPh     2-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1676                                                                             2-ClPh     2-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1677                                                                             2-ClPh     3-CF.sub.3 Ph                                                                         0 H  H   H       H  H                                   1678                                                                             2-ClPh     2-F-(4-CF.sub.3)Ph                                                                    0 H  H   H       H  H                                   1679                                                                             2-ClPh     4-CH.sub.3 OPh                                                                        0 H  H   H       H  H                                   1680                                                                             2-ClPh     5-Cl-2-pyridyl                                                                        0 H  H   H       H  H                                   1681                                                                             2-ClPh     5-Cl-2-thienyl                                                                        0 H  H   H       H  H                                   1682                                                                             2-ClPh     2-Cl-3-thienyl                                                                        0 H  H   H       H  H                                   1683                                                                             3-ClPh     2,5-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1684                                                                             3-ClPh     2,5-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1685                                                                             4-FPh      2,5-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1686                                                                             4-FPh      3-FPh   0 H  H   H       H  H                                   1687                                                                             4-FPh      2,5-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1688                                                                             4-FPh      3-ClPh  0 H  H   H       H  H                                   1689                                                                             4-FPh      4-BrPh  0 H  H   H       H  H                                   1690                                                                             4-FPh      4-IPh   0 H  H   H       H  H                                   1691                                                                             4-FPh      3,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1692                                                                             4-FPh      3,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1693                                                                             4-FPh      2,6-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1694                                                                             4-FPh      2-Cl-(4-F)Ph                                                                          0 H  H   H       H  H                                   1695                                                                             4-FPh      2,4,6-Cl.sub.3Ph                                                                      0 H  H   H       H  H                                   1696                                                                             4-FPh      2-F-(4-Cl)Ph                                                                          0 H  H   H       H  H                                   1697                                                                             4-FPh      Ph      0 H  H   H       H  H                                   1698                                                                             4-FPh      4-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1699                                                                             4-FPh      3-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1700                                                                             4-FPh      2-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1701                                                                             4-FPh      2-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1702                                                                             4-FPh      3-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1703                                                                             4-FPh      2-F-(4-CF.sub.3)Ph                                                                    0 H  H   H       H  H                                   1704                                                                             4-FPh      4-CH.sub.3 OPh                                                                        0 H  H   H       H  H                                   1705                                                                             4-FPh      5-Cl-2-pyridyl                                                                        0 H  H   H       H  H                                   1706                                                                             4-FPh      2-Cl-3-thienyl                                                                        0 H  H   H       H  H                                   1707                                                                             4-FPh      5-Cl-2-thienyl                                                                        0 H  H   H       H  H                                   1708                                                                             3-FPh      2,5-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1709                                                                             3-FPh      2,5-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1710                                                                             4-ClPh     2,5-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1711                                                                             4-ClPh     3-FPh   0 H  H   H       H  H                                   1712                                                                             4-Cl Ph    2,5-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1713                                                                             4-ClPh     3-ClPh  0 H  H   H       H  H                                   1714                                                                             4-ClPh     4-BrPh  0 H  H   H       H  H                                   1715                                                                             4-ClPh     4-IPh   0 H  H   H       H  H                                   1716                                                                             4-ClPh     3,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1717                                                                             4-ClPh     3,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1718                                                                             4-ClPh     2,6-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1719                                                                             4-ClPh     2-Cl-(4-F)Ph                                                                          0 H  H   H       H  H                                   1720                                                                             4-ClPh     2,4,6-Cl.sub.3Ph                                                                      0 H  H   H       H  H                                   1721                                                                             4-ClPh     2-F-(4-Cl)Ph                                                                          0 H  H   H       H  H                                   1722                                                                             4-ClPh     Ph      0 H  H   H       H  H                                   1723                                                                             4-ClPh     4-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1724                                                                             4-ClPh     3-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1725                                                                             4-ClPh     2-CH.sub.3Ph                                                                          0 H  H   H       H  H                                   1726                                                                             4-ClPh     2-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1727                                                                             4-ClPh     3-CF.sub.3Ph                                                                          0 H  H   H       H  H                                   1728                                                                             4-ClPh     2-F-(4-CF.sub.3)Ph                                                                    0 H  H   H       H  H                                   1729                                                                             4-ClPh     4-CH.sub. 3 OPh                                                                       0 H  H   H       H  H                                   1730                                                                             4-ClPh     5-Cl-2-pyridyl                                                                        0 H  H   H       H  H                                   1731                                                                             4-ClPh     5-Cl-2-thienyl                                                                        0 H  H   H       H  H                                   1732                                                                             4-ClPh     2-Cl-3-thienyl                                                                        0 H  H   H       H  H                                   1733                                                                             4-ClPh                                                                                    ##STR69##                                                                            0 H  H   H       H  H                                   1734                                                                             4-ClPh      .sub.-t-butyl                                                                        0 H  H   H       H  H                                   1735                                                                             4-ClPh      -n-hexyl                                                                             0 H  H   H       H  H                                   1736                                                                             4-ClPh      -n-heptyl                                                                            0 H  H   H       H  H                                   1737                                                                             4-ClPh      -n-octyl                                                                             0 H  H   H       H  H                                   1738                                                                             4-ClPh     C.sub.6 F.sub.13                                                                      0 H  H   H       H  H                                   1739                                                                             4-ClPh     C.sub.8 F.sub.17                                                                      0 H  H   H       H  H                                   1740                                                                             4-ClPh     4-pyridyl                                                                             0 H  H   H       H  H                                   1741                                                                             4-ClPh     2-pyridyl                                                                             0 H  H   H       H  H                                   1742                                                                             4-ClPh     2-thienyl                                                                             0 H  H   H       H  H                                   1743                                                                             4-ClPh     4- -n-BuPh                                                                            0 H  H   H       H  H                                   1744                                                                             4-ClPh     4-  -n-BuOPh                                                                          0 H  H   H       H  H                                   1745                                                                             4-ClPh     5-CF.sub.3 -2-pyridyl                                                                 0 H  H   H       H  H                                   1746                                                                             4-ClPh     5-CH.sub.3 SO.sub.2 -2-                                                               0 H  H   H       H  H                                                 thienyl                                                         1747                                                                             4-C.sub.2 H.sub.5Ph                                                                      4-FPh   0 H  H   H       H  H                                   1748                                                                             4-( -n-BuO)Ph                                                                            4-FPh   0 H  H   H       H  H                                   1749                                                                             2-CH.sub.3 SO.sub.2 -imida-                                                              4-FPh   0 H  H   H       H  H                                      zol-1-yl                                                                   1750                                                                             5-CH.sub.3 S-1,2,4-                                                                      4-FPh   0 H  H   H       H  H                                      triazol-1-yl                                                               1751                                                                             C.sub.6 F.sub.13                                                                         4-FPh   0 H  H   H       H  H                                   1752                                                                             C.sub.8 F.sub.17                                                                         4-FPh   0 H  H   H       H  H                                   1753                                                                             3-CH.sub.3 OPh                                                                           4-FPh   0 H  H   H       H  H                                   1754                                                                             2-CF.sub.3 -imidazol-1-yl                                                                4-FPh   0 H  H   H       H  H                                   1755                                                                             4-( .sub.-i-C.sub.3 H.sub.7 O)Ph                                                         4-FPh   0 H  H   H       H  H                                   1756                                                                             4-IPh      4-FPh   0 H  H   H       H  H                                   1757                                                                             3,4-F.sub.2Ph                                                                            4-FPh   0 H  H   H       H  H                                   1758                                                                             3,4-Cl.sub.2Ph                                                                           4-FPh   0 H  H   H       H  H                                   1759                                                                             2,6-Cl.sub.2Ph                                                                           4-FPh   0 H  H   H       H  H                                   1760                                                                             2-Cl-(4-F)Ph                                                                             4-FPh   0 H  H   H       H  H                                   1761                                                                             2,4,6-Cl.sub.3Ph                                                                         4-FPh   0 H  H   H       H  H                                   1762                                                                             4-CH.sub.3Ph                                                                             4-FPh   0 H  H   H       H  H                                   1763                                                                             3-CH.sub.3Ph                                                                             4-FPh   0 H  H   H       H  H                                   1764                                                                             2-CH.sub.3Ph                                                                             4-FPh   0 H  H   H       H  H                                   1765                                                                             2-CF.sub.3Ph                                                                             4-FPh   0 H  H   H       H  H                                   1766                                                                             3-CF.sub.3Ph                                                                             4-FPh   0 H  H   H       H  H                                   1767                                                                             4-CH.sub.3 OPh                                                                           4-FPh   0 H  H   H       H  H                                   1768                                                                             2,3-Cl.sub.2Ph                                                                           4-FPh   0 H  H   H       H  H                                   1769                                                                             3,5-Cl.sub.2Ph                                                                           4-FPh   0 H  H   H       H  H                                   1770                                                                             2,5-Cl.sub.2Ph                                                                           4-FPh   0 H  H   H       H  H                                   1771                                                                             3-BrPh     4-FPh   0 H  H   H       H  H                                   1772                                                                             4-C.sub.2 H.sub.5 OPh                                                                    4-FPh   0 H  H   H       H  H                                   1773                                                                             2,4-(CH.sub.3).sub.2Ph                                                                   4-FPh   0 H  H   H       H  H                                   1774                                                                             2,4,6-(CH.sub.3).sub.3Ph                                                                 4-FPh   0 H  H   H       H  H                                   1775                                                                             4-PhPh     4-FPh   0 H  H   H       H  H                                   1776                                                                             5-Cl-2-thienyl                                                                           4-FPh   0 H  H   H       H  H                                   1777                                                                             2-Cl-3-thienyl                                                                           4-FPh   0 H  H   H       H  H                                   1778                                                                             1-imidazoyl                                                                              4-FPh   0 H  H   H       H  H                                   1779                                                                             1H-1,2,4-triazoyl-1-yl                                                                   4-FPh   0 H  H   H       H  H                                   1780                                                                             2-pyridyl  4-FPh   0 H  H   H       H  H                                   1781                                                                             5-Cl-2-pyridyl                                                                           4-FPh   0 H  H   H       H  H                                   1782                                                                             3-pyridyl  4-FPh   0 H  H   H       H  H                                   1783                                                                             4-pyridyl  4-FPh   0 H  H   H       H  H                                   1784                                                                              -n-C.sub.4 F.sub.9                                                                      4-FPh   0 H  H   H       H  H                                   1785                                                                             4-IPh      2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1786                                                                             3,4-F.sub.2Ph                                                                            2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1787                                                                             3,4-Cl.sub.2Ph                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1788                                                                             2,6-Cl.sub.2Ph                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1789                                                                             2-Cl-(4-F)Ph                                                                             2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1790                                                                             2,4,6-Cl.sub.3Ph                                                                         2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1791                                                                             4-CH.sub.3Ph                                                                             2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1792                                                                             3-CH.sub.3Ph                                                                             2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1793                                                                             2-CH.sub.3Ph                                                                             2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1794                                                                             2-CF.sub.3Ph                                                                             2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1795                                                                             3-CF.sub.3Ph                                                                             2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1796                                                                             4-CH.sub.3 OPh                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1797                                                                             2,3-Cl.sub.2Ph                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1798                                                                             3,5-Cl.sub.2Ph                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1799                                                                             2,5-Cl.sub.2Ph                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1800                                                                             3-BrPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1801                                                                             4-C.sub.2 H.sub.5 OPh                                                                    2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1802                                                                             2,4-(CH.sub.3).sub.2Ph                                                                   2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1803                                                                             2,4,6-(CH.sub.3).sub.3Ph                                                                 2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1804                                                                             4-PhPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1805                                                                             5-Cl-2-thienyl                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1806                                                                             2-Cl-3-thienyl                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1807                                                                             1-imidazoyl                                                                              2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1808                                                                             1H-1,2,4-triazoyl-1-yl                                                                   2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1809                                                                             2-pyridyl  2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1810                                                                             5-Cl-2-pyridyl                                                                           2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1811                                                                             3-pyridyl  2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1812                                                                             4-pyridyl  2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1813                                                                              -n-C.sub.4 F.sub.9                                                                      2,4-Cl.sub.2Ph                                                                        0 H  H   H       H  H                                   1814                                                                             4-IPh      4-ClPh  0 H  H   H       H  H                                   1815                                                                             3,4-F.sub.2Ph                                                                            4-ClPh  0 H  H   H       H  H                                   1816                                                                             3,4-Cl.sub.2Ph                                                                           4-ClPh  0 H  H   H       H  H                                   1817                                                                             2,6-Cl.sub.2Ph                                                                           4-ClPh  0 H  H   H       H  H                                   1818                                                                             2-Cl-(4-F)Ph                                                                             4-ClPh  0 H  H   H       H  H                                   1819                                                                             2,4,6-Cl.sub.3Ph                                                                         4-ClPh  0 H  H   H       H  H                                   1820                                                                             4-CH.sub.3Ph                                                                             4-ClPh  0 H  H   H       H  H                                   1821                                                                             3-CH.sub.3Ph                                                                             4-ClPh  0 H  H   H       H  H                                   1822                                                                             2-CH.sub.3Ph                                                                             4-ClPh  0 H  H   H       H  H                                   1823                                                                             2-CF.sub.3Ph                                                                             4-ClPh  0 H  H   H       H  H                                   1824                                                                             3-CF.sub.3Ph                                                                             4-ClPh  0 H  H   H       H  H                                   1825                                                                             4-CH.sub.3 OPh                                                                           4-ClPh  0 H  H   H       H  H                                   1826                                                                             2,3-Cl.sub.2Ph                                                                           4-ClPh  0 H  H   H       H  H                                   1827                                                                             3,5-Cl.sub.2Ph                                                                           4-ClPh  0 H  H   H       H  H                                   1828                                                                             2,5-Cl.sub.2Ph                                                                           4-ClPh  0 H  H   H       H  H                                   1829                                                                             3-BrPh     4-ClPh  0 H  H   H       H  H                                   1830                                                                             4-EtOPh    4-ClPh  0 H  H   H       H  H                                   1831                                                                             2,4-(CH.sub.3).sub.2Ph                                                                   4-ClPh  0 H  H   H       H  H                                   1832                                                                             2,4,6-(CH.sub.3).sub.3Ph                                                                 4-ClPh  0 H  H   H       H  H                                   1833                                                                             4-PhPh     4-ClPh  0 H  H   H       H  H                                   1834                                                                             5-Cl-2-thienyl                                                                           4-ClPh  0 H  H   H       H  H                                   1835                                                                             2-Cl-3-thienyl                                                                           4-ClPh  0 H  H   H       H  H                                   1836                                                                             1-imidazoyl                                                                              4-ClPh  0 H  H   H       H  H                                   1837                                                                             1H-1,2,4-triazoyl-1-yl                                                                   4-ClPh  0 H  H   H       H  H                                   1838                                                                             2-pyridyl  4-ClPh  0 H  H   H       H  H                                   1839                                                                             5-Cl-2-pyridyl                                                                           4-ClPh  0 H  H   H       H  H                                   1840                                                                             3-pyridyl  4-ClPh  0 H  H   H       H  H                                   1841                                                                             4-pyridyl  4-ClPh  0 H  H   H       H  H                                   1842                                                                              -n-C.sub.4 F.sub.9                                                                      4-ClPh  0 H  H   H       H  H                                   1843                                                                             4-IPh      2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1844                                                                             3,4-F.sub.2Ph                                                                            2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1845                                                                             3,4-Cl.sub.2Ph                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1846                                                                             2,6-Cl.sub.2Ph                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1847                                                                             2-Cl-(4-F)Ph                                                                             2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1848                                                                             2,4,6-Cl.sub.3Ph                                                                         2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1849                                                                             4-CH.sub.3Ph                                                                             2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1850                                                                             3-CH.sub.3Ph                                                                             2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1851                                                                             2-CH.sub.3Ph                                                                             2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1852                                                                             2-CF.sub.3Ph                                                                             2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1853                                                                             3-CF.sub.3Ph                                                                             2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1854                                                                             4-CH.sub.3 OPh                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1855                                                                             2,3-Cl.sub.2Ph                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1856                                                                             3,5-Cl.sub.2Ph                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1857                                                                             2,5-Cl.sub.2Ph                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1858                                                                             3-BrPh     2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1859                                                                             4-C.sub.2 H.sub.5 OPh                                                                    2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1860                                                                             2,4-(CH.sub.3).sub.2Ph                                                                   2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1861                                                                             2,4,6-(CH.sub.3).sub.3Ph                                                                 2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1862                                                                             4-PhPh     2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1863                                                                             5-Cl-2-thienyl                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1864                                                                             2-Cl-3-thienyl                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1865                                                                             1-imidazoyl                                                                              2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1866                                                                             1H-1,2,4-triazoyl-1-yl                                                                   2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1867                                                                             2-pyridyl  2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1868                                                                             5-Cl-2-pyridyl                                                                           2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1869                                                                             3-pyridyl  2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1870                                                                             4-pyridyl  2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1871                                                                              -n-C.sub.4 F.sub.9                                                                      2,4-F.sub.2Ph                                                                         0 H  H   H       H  H                                   1872                                                                             4-FPh      4-FPh   0 H  H   H       CH.sub.3                                                                         H                                   1873                                                                             4-FPh      4-FPh   0 H  H   H       CH.sub.3                                                                         CH.sub.3                            1874                                                                             4-FPh      4-FPh   0 H  H   H       F  H                                   1875                                                                             4-FPh      4-FPh   0 H  H   H       F  CH.sub.3                            1876                                                                             4-FPh      4-FPh   0 H  H   H       F  F                                   1877                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       CH.sub.3                                                                         H                                   1878                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       CH.sub.3                                                                         CH.sub.3                            1879                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       F  H                                   1880                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       F  CH.sub.3                            1881                                                                             4-ClPh     2,4-Cl.sub.2Ph                                                                        0 H  H   H       F  F                                   1882                                                                             2-ClPh     4-ClPh  0 H  H   H       CH.sub.3                                                                         H                                   1883                                                                             2-ClPh     4-ClPh  0 H  H   H       CH.sub.3                                                                         CH.sub.3                            1884                                                                             2-ClPh     4-ClPh  0 H  H   H       F  H                                   1885                                                                             2-ClPh     4-ClPh  0 H  H   H       F  CH.sub.3                            1886                                                                             2-ClPh     4-ClPh  0 H  H   H       F  F                                   1887                                                                             Ph         4-FPh   0 H  H   H       CH.sub.3                                                                         H                                   1888                                                                             Ph         4-FPh   0 H  H   H       CH.sub.3                                                                         CH.sub.3                            1889                                                                             Ph         4-FPh   0 H  H   H       F  H                                   1890                                                                             Ph         4-FPh   0 H  H   H       F  CH.sub.3                            1891                                                                             Ph         4-FPh   0 H  H   H       F  F                                   __________________________________________________________________________     .sup.a NMR: (CDCl.sub.3 )δ 2.7(m, 2H), 4.4(1/2 of ABq, J=12, 1H),       4.9(1/2 of ABq, J=12, 1H), 5.0(br s, 1H, 0H), 6.7(m, 2H), 7.0(m, 2H),         7.4(m, 3H), 7.8(s, 1H), 8.0(s, 1H).                                      

EXAMPLE 19302-(2,4-Difluorophenyl)-3-(2-chlorophenyl)-1-(1B-1,2,4-imidazol-1-yl)-3-buten-2-ol

A mixture of 10.2 g (0.035 mol) of2-(2,4-difluorophenyl)-2-[1-(2-chlorophenyl)ethenyl]oxirane; 6.20 g(0.091 mol) of imidazole and 12.44 g (0.091 mol) of potassium carbonatein 100 mL of DMSO was heated overnight at 100°, then cooled and pouredinto 800 mL of H₂ O. The aqueous mixture was extracted with 4×500 mL Et₂O, and the organic extracts were washed with water (2×) and brine, driedover MgSO₄ and evaporated to give 7.8 g of a yellow-brown solid. Flashchromatography and trituration with Et₂ O gave 4.0 g of a white powder,mp 139°-142°; NMR: (CDCl₃) δ 3.9 (br, OH), 4.2 (1/2 of ABq, 1H), 4.7(1/2 of ABq, 1H, CH₂ -imidazole), 5.3 (s, 1H, vinyl), 5.5 (s, 1H,vinyl), 6.7 (m, 4H), 7.0-7.5 (m, 6H); IR (nujol) 3400-2600 (br), 1614,1512, 1501, 1111, 1075, 852, 819, 768, 743, 623 cm⁻¹.

The compounds shown in Table 4A were prepared or can be prepared by themethods described above.

                                      TABLE 4A                                    __________________________________________________________________________     ##STR70##                                                                    Ex.                                                                           No. A      B      n  R  R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                          R.sup.4                                                                          M.P. °C.                           __________________________________________________________________________    1892                                                                              Ph     Ph     0  H  H  H  H                                               1893                                                                              Ph     2-FPh  0  H  H  H  H                                               1894                                                                              Ph     4-FPh  0  H  H  H  H     (oil).sup.a                               1895                                                                              Ph     2,4-F.sub.2Ph                                                                        0  H  H  H  H     157-158                                   1896                                                                              Ph     2-ClPh 0  H  H  H  H                                               1897                                                                              Ph     4-ClPh 0  H  H  H  H                                               1898                                                                              Ph     2,4-Cl.sub.2Ph                                                                       0  H  H  H  H                                               1899                                                                              2-FPh  Ph     0  H  H  H  H                                               1900                                                                              2-FPh  2-FPh  0  H  H  H  H                                               1901                                                                              2-FPh  4-FPh  0  H  H  H  H                                               1902                                                                              2-FPh  2,4-F.sub.2Ph                                                                        0  H  H  H  H                                               1903                                                                              2-FPh  2-ClPh 0  H  H  H  H                                               1904                                                                              2-FPh  4-ClPh 0  H  H  H  H                                               1905                                                                              2-FPh  2,4-Cl.sub.2Ph                                                                       0  H  H  H  H                                               1906                                                                              3-FPh  Ph     0  H  H  H  H                                               1907                                                                              3-FPh  2-FPh  0  H  H  H  H                                               1908                                                                              3-FPh  4-FPh  0  H  H  H  H                                               1909                                                                              3-FPh  2,4-F.sub.2Ph                                                                        0  H  H  H  H                                               1910                                                                              3-FPh  2-ClPh 0  H  H  H  H                                               1911                                                                              3-FPh  4-ClPh 0  H  H  H  H                                               1912                                                                              3-FPh  2,4-Cl.sub.2Ph                                                                       0  H  H  H  H                                               1913                                                                              4-FPh  Ph     0  H  H  H  H                                               1914                                                                              4-FPh  2-FPh  0  H  H  H  H     159-160                                   1915                                                                              4-FPh  4-FPh  0  H  H  H  H     175-177                                   1916                                                                              4-FPh  2,4-F.sub.2Ph                                                                        0  H  H  H  H     194-197                                   1917                                                                              4-FPh  2-ClPh 0  H  H  H  H                                               1918                                                                              4-FPh  4-ClPh 0  H  H  H  H                                               1919                                                                              4-FPh  2,4-Cl.sub.2Ph                                                                       0  H  H  H  H     200-215 (60%                                                                  pure)                                     1920                                                                              2,4-F.sub.2Ph                                                                        Ph     0  H  H  H  H                                               1921                                                                              2,4-F.sub.2Ph                                                                        2-FPh  0  H  H  H  H                                               1922                                                                              2,4-F.sub.2Ph                                                                        4-FPh  0  H  H  H  H                                               1923                                                                              2,4-F.sub.2Ph                                                                        2,4-F.sub.2Ph                                                                        0  H  H  H  H                                               1924                                                                              2,4-F.sub.2Ph                                                                        2-ClPh 0  H  H  H  H                                               1925                                                                              2,4-F.sub.2Ph                                                                        4-ClPh 0  H  H  H  H                                               1926                                                                              2,4-F.sub.2Ph                                                                        2,4-Cl.sub.2Ph                                                                       0  H  H  H  H                                               1927                                                                              2-ClPh Ph     0  H  H  H  H                                               1928                                                                              2-ClPh 2-FPh  0  H  H  H  H                                               1929                                                                              2-ClPh 4-FPh  0  H  H  H  H                                               1930                                                                              2-ClPh 2,4-F.sub.2Ph                                                                        0  H  H  H  H     139-142                                                                       (HCl salt                                                                     215-217)                                  1931                                                                              2-ClPh 2-ClPh 0  H  H  H  H                                               1932                                                                              2-ClPh 4-ClPh 0  H  H  H  H     160-162                                                                       (HCl salt                                                                     170-173)                                  1933                                                                              2-ClPh 2,4-Cl.sub.2 Ph                                                                      0  H  H  H  H                                               1934                                                                              3-ClPh Ph     0  H  H  H  H  H                                            1935                                                                              3-ClPh 2-FPh  0  H  H  H  H  H                                            1936                                                                              3-ClPh 4-FPh  0  H  H  H  H  H                                            1937                                                                              3-ClPh 2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1938                                                                              3-ClPh 2-ClPh 0  H  H  H  H  H                                            1939                                                                              3-ClPh 4-ClPh 0  H  H  H  H  H                                            1940                                                                              3-ClPh 2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            1941                                                                              4-ClPh Ph     0  H  H  H  H  H                                            1942                                                                              4-ClPh 2-FPh  0  H  H  H  H  H                                            1943                                                                              4-ClPh 4-FPh  0  H  H  H  H  H                                            1944                                                                              4-ClPh 2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1945                                                                              4-ClPh 2-ClPh 0  H  H  H  H  H                                            1946                                                                              4-ClPh 4-ClPh 0  H  H  H  H  H  179-181                                   1947                                                                              4-ClPh 2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            1948                                                                              2,4-Cl.sub.2Ph                                                                       Ph     0  H  H  H  H  H                                            1949                                                                              2,4-Cl.sub.2Ph                                                                       2-FPh  0  H  H  H  H  H                                            1950                                                                              2,4-Cl.sub.2Ph                                                                       4-FPh  0  H  H  H  H  H                                            1951                                                                              2,4-Cl.sub.2Ph                                                                       2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1952                                                                              2,4-Cl.sub.2Ph                                                                       2-ClPh 0  H  H  H  H  H                                            1953                                                                              2,4-Cl.sub.2Ph                                                                       4-ClPh 0  H  H  H  H  H                                            1954                                                                              2,4-Cl.sub.2Ph                                                                       2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            1955                                                                              2-BrPh Ph     0  H  H  H  H  H                                            1956                                                                              2-BrPh 2-FPh  0  H  H  H  H  H                                            1957                                                                              2-BrPh 4-FPh  0  H  H  H  H  H                                            1958                                                                              2-BrPh 2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1959                                                                              2-BrPh 2-ClPh 0  H  H  H  H  H                                            1960                                                                              2-BrPh 4-ClPh 0  H  H  H  H  H                                            1961                                                                              2-BrPh 2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            1962                                                                              3-BrPh Ph     0  H  H  H  H  H                                            1963                                                                              3-BrPh 2-FPh  0  H  H  H  H  H                                            1964                                                                              3-BrPh 4-FPh  0  H  H  H  H  H                                            1965                                                                              3-BrPh 2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1966                                                                              3-BrPh 2-ClPh 0  H  H  H  H  H                                            1967                                                                              3-BrPh 4-ClPh 0  H  H  H  H  H                                            1968                                                                              3-BrPh 2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            1969                                                                              4-BrPh Ph     0  H  H  H  H  H                                            1970                                                                              4-BrPh 2-FPh  0  H  H  H  H  H                                            1971                                                                              4-BrPh 4-FPh  0  H  H  H  H  H                                            1972                                                                              4-BrPh 2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1973                                                                              4-BrPh 2-ClPh 0  H  H  H  H  H                                            1974                                                                              4-BrPh 4-ClPh 0  H  H  H  H  H                                            1975                                                                              4-BrPh 2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            1976                                                                              2-CF.sub.3Ph                                                                         Ph     0  H  H  H  H  H  177-179                                   1977                                                                              2-CF.sub.3Ph                                                                         2-FPh  0  H  H  H  H  H  185-187                                   1978                                                                              2-CF.sub.3Ph                                                                         4-FPh  0  H  H  H  H  H  170-172                                   1979                                                                              2-CF.sub.3Ph                                                                         2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1980                                                                              2-CF.sub.3Ph                                                                         2-ClPh 0  H  H  H  H  H                                            1981                                                                              2-CF.sub.3Ph                                                                         4-ClPh 0  H  H  H  H  H  159-161                                   1982                                                                              2-CF.sub.3Ph                                                                         2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            1983                                                                              3-CF.sub.3Ph                                                                         Ph     0  H  H  H  H  H                                            1984                                                                              3-CF.sub.3Ph                                                                         2-FPh  0  H  H  H  H  H                                            1985                                                                              3-CF.sub.3Ph                                                                         4-FPh  0  H  H  H  H  H                                            1986                                                                              3-CF.sub.3Ph                                                                         2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1987                                                                              3-CF.sub.3Ph                                                                         2-ClPh 0  H  H  H  H  H                                            1988                                                                              3-CF.sub.3Ph                                                                         4-ClPh 0  H  H  H  H  H                                            1989                                                                              3-CF.sub.3Ph                                                                         2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            1990                                                                              4-CF.sub.3Ph                                                                         Ph     0  H  H  H  H  H                                            1991                                                                              4-CF.sub.3Ph                                                                         2-FPh  0  H  H  H  H  H                                            1992                                                                              4-CF.sub.3Ph                                                                         4-FPh  0  H  H  H  H  H                                            1993                                                                              4-CF.sub.3Ph                                                                         2,4-F.sub.2Ph                                                                        0  H  H  H  H  H                                            1994                                                                              4-CF.sub.3Ph                                                                         2-ClPh 0  H  H  H  H  H                                            1995                                                                              4-CF.sub.3Ph                                                                         4-ClPh 0  H  H  H  H  H                                            1996                                                                              4-CF.sub.3Ph                                                                         2,4-Cl.sub.2Ph                                                                       0  H  H  H  H  H                                            __________________________________________________________________________     .sup.a NMR: (CDCl.sub.3) δ 4.5 (ABq, 2H), 4.8 (br s, 1H), 5.5 (two      s, 2H), 6.7 (s, 1H), 6.9 (s, 1H), 7.0-7.6 (m, 10H)                       

PHARMACEUTICAL UTILITY

In vitro activity (Table 5) is expressed in terms of the minimalinhibitory concentration (MIC) of the test compound which inhibits thegrowth of yeasts and fungi.

The target organisms, Candida albicans ATCC 11651 and Aspergillusfumigatus ATCC 28214 are standardized, [V. Bezjak, J. Clinical Micro.,21, 509-512 (1984)] to a concentration of 10⁷ organisms/ml andmaintained at -70° until use. Test compounds are solublized in dimethylsulfoxide (DMSO) and diluted in Eagle's Minimum Essential Medium (EMEM)broth to achieve a final concentration of 200 μg/ml. Stock solutions ofstandard antifungal agents are stored at -70° and diluted in EMEM asrequired.

The in vitro assay utilizes a microtiter broth dilution technique [L.Polonelli and G. Morace, Mycopathologia, 86, 21-28 (1984)] and C.Hughes, et. al. Antimicrob. Ag. and Chemo., 25, 560-562 (1984)]. Testcompounds are serially diluted in EMEM to give graded concentrationsranging from 100 to 0.4 μg/ml. The appropriate wells are inoculated withthe required organism (C. albicans at 1×10⁴ organisms/ml and A.fumigatus at 5×10⁵ organisms/ml) and the assay incubated at 30° for 24hours. The extent of fungal growth is determined at an optical densityequal to 540 nm using a scanning spectrophotometer (Flow® MCC) and MICvalues, representing the minimal concentration of a compound whichinhibited growth, are determined, [V. Grenta, et al. Antimicrob. Ag. andChemo., 22, 151-153 (1982)].

The in vivo activity of test compounds is based on the percent (%)survival of infected animals receiving test or standard agent comparedto that in an infected untreated group (Table 6). The in vivo assays arechronic systemic infections lethal to mice within 7 days post infection,[J. Barnes, et al. Lab Investigation, 49, 460-467 (1963), and T. Rogersand E. Balish, Infection and Immunity, 14, 33-38 (1976)].

Candida albicans ATCC 11651, from a frozen stock culture (10⁹organisms/ml) maintained at -70°, is diluted in saline to 1×10⁷organisms/ml and 0.2 ml inoculated intravenously (caudal vein) into 20.0gm CF-1 female mice (Charles River).

Test compounds are routinely solubilized in 0.25% (w/v) methylcellulose(Methocel®) but for those compounds difficult to solubilize 10% (w/v)Emulophor® (EL620 GAF Corp.) is used. The standard antifungal agents,amphotericin B (Fungizone®) in water and ketoconazole (Nizoral®) inMethocel®, are administered at 1.0 mg/kg/day and 150 mg/kg/day,respectively.

In a primary assay, mice (10 per group) are infected with C. albicans,and receive test compounds at 50 or 150 mg/kg/day via the subcutaneousroute. Animals are dosed with the test compound at 1 and 6 hourspost-infection and then once daily for the next three days.

Compounds which protect ≧70% of the infected animals for 14 days at adose 150 mg/kg/day or less are viewed as active.

                  TABLE 5                                                         ______________________________________                                        In Vitro Antifungal Results                                                    ##STR71##                                                                                  MIC values (μg/ml)                                                         C. albicans                                                                           A. fumigatus                                            ______________________________________                                        Example Number                                                                1                   ≦0.01                                                                            6.3                                             1      HCl salt     0.05      12.5                                            2                   ≦0.4                                                                             1.6                                             3                   ≦0.4                                                                             50                                              4                   0.03      0.8                                             6                   1.6       25                                              10                  1.6       25                                              15                  0.1       50                                              16                  0.03      6.3                                             17                  0.03      12.5                                            25                  1.6       25                                              26                  ≦0.4                                                                             12.5                                            26     HCl salt     0.03      0.4                                             27                  ≦0.4                                                                             12.5                                            28                  0.03      1.6                                             32                  ≦0.4                                                                             1.6                                             33                  0.03      0.03                                            34                  0.03      3.2                                             34     HCl salt     0.03      1.6                                             35                  0.03      0.1                                             35     HCl salt     0.03      ≦0.2                                     39                  0.4       25                                              40                  0.4       3.2                                             41                  0.4       50                                              42                  0.03      6.3                                             47                  0.03      1.6                                             49                  0.03      12.5                                            50                  0.1       0.8                                             51                  0.03      3.2                                             52                  0.03      0.4                                             52     HCl salt     0.03      0.4                                             65                  0.2       100                                             67                  0.03      100                                             85                  ≦0.4                                                                             12.5                                            94                  0.4       50                                              99                  0.05      6.3                                             100                 0.03      3.2                                             101                 0.03      12.5                                            114                 0.4       50                                              117                 0.4       100                                             163                 0.03      12.5                                            164                 0.03      1.6                                             170                 1.6       100                                             177                 3.2       >100                                            208                 1.6       50                                              286                 0.4       25                                              291                 0.2       100                                             359                 0.4       50                                              360                 0.8       100                                             361                 0.8       25                                              363                 100       100                                             447                 3.2       N.T.                                            449                 ≦0.4                                                                             N.T.                                            450                 >100      N.T.                                            451                 12.5      N.T.                                            452                 >100      N.T.                                            453                 1.6       >100                                            454                 100       >100                                            455                 25        N.T.                                            477                 >100      N.T.                                            594                 0.8       0.8                                             594    HCl salt     0.03      0.4                                             596                 0.05      0.4                                             603                 0.1       >100                                            605                 0.2       100                                             608                 0.4       6.3                                             620                 0.03      0.05                                            622                 0.03      0.1                                             627                 0.03      25                                              644                 0.03      0.4                                             646                 0.03      0.4                                             651                 0.8       100                                             656                 ≦0.4                                                                             12.5                                            657                 0.4       100                                             661                 1.6       100                                             667                 6.3       25                                              668                 0.4       50                                              669                 0.03      0.8                                             671                 0.03      0.2                                             675                 0.1       25                                              685                 0.8       100                                             699                 50        100                                             721                 0.4       12.5                                            724                 0.4       0.4                                             726                 0.8       6.3                                             815                 0.03      >100                                            905                 0.04      100                                             1258                1.6       >100                                            1260                0.8       >100                                            1276                0.03      1.6                                             1276a               3.2       100                                             1277                0.03      6.3                                             1277   HCl salt     0.03      3.2                                             1277a               6.3       100                                             1278                ≦0.4                                                                             >100                                            1300                ≦0.4                                                                             6.3                                             1377                1.6       100                                             1451                >100      >100                                            1459                >100      >100                                            1487                0.4       6.3                                             1527                0.4       6.3                                             Standards*                                                                    Amphotericin B  0.33 ± 0.2                                                                           1.4 ± 0.5                                        Nystatin        1.3 ± 0                                                                              3.0 ± 1.0                                        5-Fluorocytosine                                                                              0.14 ± 0.1                                                                           5.7 ± 4.0                                        Ketoconazole    ≦0.1                                                                             11.0 ± 5.0                                       Miconazole      ≦0.1                                                                             1.3 ± 0                                          ______________________________________                                         *MIC values of the standard drugs are the mean of five determinations         ± Standard deviation                                                  

                  TABLE 6                                                         ______________________________________                                        In Vivo Antifungal Results                                                    % Survival (150 mg/kg per day)                                                Primary Assay                                                                            Days                                                                          7         14     21                                                ______________________________________                                        Ex. No.                                                                         1          100         100    80                                              2          100         100    80                                              3          100         100    60                                              4          100         50     N.T.                                            6           50         10      0                                             10           20         10      0                                             15          100         90     60                                             16          100         100    100                                            17          100         90     70                                             25          100         100    50                                             26          100         100    100                                            26 salt     100         90     80                                             27          100         100    100                                            28          100         90     N.T.                                           32          100         90     50                                             33          100         100    100                                            34          100         100    100                                            34 salt     100         100    100                                            35          100         100    90                                             35 salt     100         100    70                                             39          100         80     N.T.                                           40          100         100    N.T.                                           41          100         100    N.T.                                           42           80         80     50                                             47           90         80     30                                             49          100         90     60                                             50          100         90     50                                             51          100         100    80                                             52          100         100    90                                             52 salt     100         100    90                                             55          100         70     50                                             65          100         70     50                                             67          100         100    100                                            85          100         80     70                                             94          100         40     10                                             99          100         100    40                                             100         100         50     30                                             101         100         90     60                                             114          70         10     10                                             117          60          0      0                                             163          90         60     40                                             164         100         80     70                                             208          0           0      0                                             286         100         50     20                                             359         100         80     80                                             360         100         60     40                                             361         100         100    90                                             363          10          0      0                                             453          60         40     30                                             594          70         10      0                                             596          70         60     40                                             603          10          0      0                                             608         100         70     20                                             620         100         100    90                                             622         100         100    100                                            627          0           0      0                                             644          80         70     50                                             646         100         100    70                                             651         100         50     20                                              656        100         90     40                                             657          0           0      0                                             661          50         20      0                                             667          10          0      0                                             668          70         10      0                                             669         100         100    100                                            671         100         100    60                                             675         100         60      0                                             685          30         10      0                                             721         100         30     30                                             724         100         90     40                                             725          90         90     40                                             726         100         80     10                                             905          80         50     20                                            1276         100         70     50                                            1276a         0           0      0                                            1277         100         100    90                                            1277a         80          0      0                                            1278          0           0      0                                            1487         100         100    70                                            1527         100         70     20                                            Standards                                                                     Amphotericin B                                                                             100         100    100                                           Ketoconazole 100         80     50                                            ______________________________________                                         N.T.: Not Tested                                                         

DOSAGE FORMS

The antimycotic agents of this invention can be administered by anymeans that effects contact of the active ingredient with the agent'ssite of action in the body. The compounds can be administered by anyconventional means available for use in conjunction withpharmaceuticals, either as individual therapeutic agents or in acombination of therapeutic agents. They can be administered alone, butare generally administered with a pharmaceutical carrier selected on thebasis of the chosen route of administration and standard pharmaceuticalpractice.

The dosage administered will, of course, vary depending on the use andknown factors such as the pharmacodynamic characteristics of theparticular agent, and its mode and route of administration: age, health,and weight of the recipient; nature and extent of symptoms, kind ofconcurrent treatment, frequency of treatment, and the effect desired.

Dosage forms (compositions) suitable for administration contain fromabout 200 milligram to about 2000 milligrams of active ingredient perunit. In these pharmaceutical compositions, the active ingredient willordinarily be present in an amount of about 0.5-95% by weight based onthe total weight of the composition. For use in the treatment of saiddiseases, a daily dose of active ingredient can be about 10 to 50milligrams per kilogram of body weight.

The composition of the invention may be in a conventional pharmaceuticalform suitable for oral administration, for example, a tablet, a capsule,an emulsion or an aqueous or oily solution or suspension, or suitablefor topical application, for example a cream, ointment or gel. It canalso be administered parenterally in sterile liquid dosage forms.

Gelatin capsules contain the active ingredient and powdered carriers,such as lactose, starch, cellulose derivatives, magnesium stearate,stearic acid and the like. Similar diluents can be used to makecompressed tablets. Both tablets and capsules can be manufactured assustained release products to provide for continuos release ofmedication over a period of hours. Compressed tablets can be sugarcoated or film coated to mask any unpleasant taste and protect thetablet from the atmosphere, or enteric coated for selectivedisintegration in the gastrointestinal tract.

The pharmaceutical compositions which are ointments, creams and gelscan, for example, contain the usual diluents, e.g. animal and vegetablefats, waxes, paraffins, starch, tragacanth, cellulose derivatives,polyethylene glycols, silicones, bentonites, silicic acid, talc and sincoxide or mixture of these substances.

In general, water, a suitable oil, saline, aqueous dextrose (glucose),and related sugar solutions and glycols such as propylene glycol orpolyethylene glycols are suitable carriers for parental solutions.Solutions for parenteral administration preferably contain a watersoluble salt of the active ingredient, suitable stabilizing agents, andif necessary, buffer substances. Antioxidizing agents such as sodiumbisulfite, sodium sulfite, or ascorbic acid, either alone or combined,are suitable stabilizing agents.

All the pharmaceutical compositions according to the invention can alsocontain coloring and flavoring to increase patient acceptance.

Also used are citric acid and its salts and sodium EDTA. In addition,parenteral solutions can contain preservatives, such as benzalkoniumchloride, methyl or propyl-paraben, and chlorobutanol.

Suitable pharmaceutical carriers are described in Remington'sPharmaceutical Sciences, A. Osol, a standard reference text in thisfield.

Useful pharmaceutical dosage forms for administration of the compoundsof this invention can be illustrated as follows:

Capsules

A large number of unit capsules are prepared by filling standardtwo-piece hard gelatin capsules each with 100 milligrams of powderedactive ingredient, 150 milligrams of lactose, 50 milligrams ofcellulose, and 6 milligrams magnesium stearate.

Soft Gelatin Capsules

A mixture of active ingredient is a digestable oil such as soybean oil,cottonseed oil or olive oil is prepared and injected by means of apositive displacement pump into gelatin to form soft gelatin capsulescontaining 100 milligrams of the active ingredient. The capsules arewashed and dried.

Tablets

A large number of tablets are prepared by conventional procedures sothat the dosage unit is 100 milligrams of active ingredient, 0.2milligrams of colloidal silicon dioxide, 5 milligrams of magnesiumstearate, 275 milligrams of microcrystalline cellulose, 11 milligrams ofstarch and 98.8 milligrams of lactose. Appropriate coatings may beapplied to increase palatability or delay absorption.

Injectable

A parenteral composition suitable for administration by injection isprepared by stirring 1.5% by weight of active ingredient in 10% byvolume propylene glycol. The solution is made to volume with water forinjection and sterilized.

Suspension

An aqueous suspension is prepared for oral administration so that each 5milliliters contain 100 milligrams of finely divided active ingredient,100 milligrams of sodium carboxymethyl cellulose, 5 milligrams of sodiumbenzoate, 1.0 grams of sorbitol solution, U.S.P., and 0.025 millilitersof vanillin.

Cream

A cream for topical application is prepared by incorporating 100milligrams of the finely pulverized active ingredient in 5 grams of acream base which comprises 40% white petrolatum, 3% microcrystallinewax, 10% lanolin, 5% Span®20, 0.3% Tween®20 and 41.7% water.

Agricultural Formulations

The compounds of this invention when used for agricultural purposes willgenerally be used in formulation with a liquid or solid diluent or withan organic solvent. Useful formulations of the compounds of Formula Ican be prepared in conventional ways. They include dusts, granules,pellets, solutions, emulsions, wettable powders, emulsifiableconcentrates and the like. Many of these may be applied directly.Sprayable formulations can be extended in suitable media and used atspray volumes of from about one to several hundred liters per hectare.High strength compositions are primarily used as intermediates forfurther formulation. The formulations, broadly, contain about 1% to 99%by weight of active ingredient(s) and at least one of a) about 0.1% to35% surfactant(s) and b) about 5% to 99% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

    ______________________________________                                                    Percent by Weight                                                             Active                                                                        Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             5-50     40-95     0-35                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspensions                                                                         10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                         1-95      5-99     0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                    

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J. The more absorptive diluents are preferred for thewettable powders and the denser ones for dusts. Typical liquid diluentsand solvents are described in Marsden, "Solvents Guide", 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well asSisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publ.Co., Inc., New York, 1964, list surfactants and recommended used. Allformulations can contain minor amounts of additives to reduce foam,caking, corrosion, microbiological growth, etc. Preferably, ingredientsshould be approved by the U.S. Environmental Protection Agency for theuse intended.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 4th Edn., McGraw-Hill, N.Y., 1963, pp. 8-59ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, Line 16through Col. 7, Line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, Line43 through Col. 7, Line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167, 169-192.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,Line 66 through Col. 5, Line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Edn. BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

Examples of useful formulations of compounds of the present inventionare as follows.

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        2-(2,4-difluorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-                                                    80%                                               triazol-1-yl)-3-buten-1-ol; and the (S) enantiomer                            thereof                                                                       sodium alkylnaphthalenesulfonate                                                                          2%                                                sodium ligninsulfonate      2%                                                synthetic amorphous silica  3%                                                kaolinite                   13%                                               ______________________________________                                    

The ingredients are blended, hammer-milled, re-blended and packaged.

    ______________________________________                                        Granule                                                                       ______________________________________                                        wettable powder of above example                                                                     15%                                                    gypsum                 69%                                                    potassium sulfate      16%                                                    ______________________________________                                    

The ingredients are blended in a rotating or fluid bed mixer and watersprayed on to accomplish granulation. When most of the material hasreached the desired range of 1.0 to 0.42 mm. (U.S.S. No. 18 to 40sieves), the granules are removed, dried, and screened. Oversizematerial is crushed to produce additional material in the desired range.

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        2-(2-fluorophenyl)-3-(4-fluorophenyl)-1-                                                              98.5%                                                 (1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and                                     the (S) enantiomer thereof                                                    silica aerogel          0.5%                                                  synthetic amorphous fine silica                                                                       1.0%                                                  ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce ahigh strength concentrate essentially all passing a U.S.S. No. 50 sieve(0.3 mm openings). This material may then be formulated in a variety ofways.

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        2-(2,4-difluorophenyl)-3-phenyl-1-                                                                    25%                                                   1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and                                      the (S) enantiomer thereof                                                    hydrated attapulgite    3%                                                    crude calcium ligninsulfonate                                                                         10%                                                   sodium dihydrogen phosphate                                                                           0.5%                                                  water                   61.5%                                                 ______________________________________                                    

The ingredients are ground together in a ball, sand, or roller milluntil the solid particles have been reduced to diameters under 10microns.

    ______________________________________                                        Solution                                                                      ______________________________________                                        2-(2,4-difluorophenyl)-3-(4-chlorophenyl)-                                                             30%                                                  1-(1H-1,2,4-traizol-1-yl)-3-buten-2-ol; and                                   the (S) enantiomer thereof                                                    dimethylformamide        70%                                                  ______________________________________                                    

The ingredients are combined and stirred to produce a solution, whichcan be used for low volume applications.

    ______________________________________                                        Emulsifiable Concentrate                                                      ______________________________________                                        2-(2,4-difluorophenyl)-3-(4-fluorophenyl)-                                                             15%                                                  1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and                                   the (S) enantiomer thereof                                                    blend of calcium sulfonates                                                                            25%                                                  and nonionic surfactants                                                      xylene                   60%                                                  ______________________________________                                    

The ingredients are combined and stirred until the active is dissolved.A fine screen filter is included in packaging operation to insure theabsence of any extraneous undissolved material in the product.

Utility

The compounds of this invention are useful as plant disease controlagents. They are effective in controlling a broad spectrum of plantdiseases, particularly foliar pathogens of ornamental, vegetable, field,cereal and fruit crops, such as Puccinia recondita, Erysiphecichoracearum, Erysiphe graminis, Venturia inaequalis, Cercosporaarachidicola, and Monilinia fructicola, Rhizoctonia solani, Pyriculariaoryzae, Botrytis cinerea, Pseudocercosporella herpotrichlorides, andCercosporidium personatum. They also control seed pathogens.

Disease control is ordinarily accomplished by applying an effectiveamount of the compound either pre- or post-infection to the portion ofthe plant to be protected, such as the roots, stems, foliage, fruit,seeds, tubers or bulbs, or to the media (soil or sand) in which theplants to be protected are growing. The compound may also be applied tothe seed from which the plants to be protected are to be grown.

Rates of application for these compounds can be influenced by manyfactors of the environment and should be determined under actual useconditions. Foliage can normally be protected when treated at a rate offrom less than 1 g/ha to 5000 g/ha of active ingredient. Plants growingin soil treated at a concentration from 0.1 to about 20 kg/ha can beprotected from disease. Seed and seedlings can normally be protectedwhen seed is treated at a rate of from 0.06 to about 3 grams perkilogram of seed.

The compounds of this invention can be mixed with fungicides,bactericides, acaricides, nematicides, insecticides, or otherbiologically active compounds in order to achieve desired results with aminimum expenditure of time, effort and material. Amounts of thesebiologically active materials added for each part by weight of thecomposition of this invention may vary from 0.05 to 25 parts by weight.Suitable agents of this type are well-known to those skilled in the art.Some are listed below:

Fungicides

methyl 2-benzimidazolecarbamate (carbendazim)

tetramethylthiuram disulfide (thiuram)

n-dodecylguanidine acetate (dodine)

manganese ethylenebisdithiocarbamate (maneb)

1,4-dichloro-2,5-dimethoxybenzene (chloroneb)methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl)

2-cyano-N-ethylcarbamoyl-2-methoxyiminoacetamide (cymoxanil)

N-trichloromethylthiotetrahydrophthalamide (captan)

N-trichloromethylthiophthalimide (folpet)

dimethyl 4,4'-(o-phenylene)bis(3-thioallophanate)(thiophanate-methyl)

2-(thiazol-4-yl)benzimidazole (thiabendazole)

aluminum tris(O-ethyl phosphonate)(phosethyl aluminum)

tetrachloroisophthalonitrile (chloroethalonil)

2,6-dichloro-4-nitroaniline (dichloran)

N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methyl ester (metalaxyl)

cis-N-[1,1,2,2-tetrachloroethyl)thio]cyclohex-4-ene-1,2-dicarbioximide(captafol)

3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide (iprodione)

3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione(vinclozolin)

kasugamycin

O-ethyl-S,S-diphenylphosphorodithioate (edifenphos)

4-(3-(4-(1,1-dimethyl-ethyl)phenyl)-2-methyl)propyl-2,6-dimethylmorpholine(Fenpropimorph)

4-(3-4(1,1-dimethyl-ethyl)phenyl)-2-methyl)propylpiperidine(Fenpropidine).

Bactericides

tribasic copper sulfate

streptomycin sulfate

oxytetracycline.

Acaricides

senecioic acid, ester with 2-sec-butyl-4,6-dinitrophenol (binapacryl)

6-methyl-1,3-dithiolo[2,3-B]quinonolin-2-one (oxythioquinox)

2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethanol(dicofol)

bis(pentachloro-2,4-cyclopentadien-1-yl)(dienochlor)

tricyclohexyltin hydroxide (cyhexatin)

hexakis(2-methyl-2-phenylpropyl)distannoxane (fenbutin oxide).

Nematicides

2-[diethoxyphosphinylimino]-1,3-diethietane (fosthietan)

S-methyl-1-(dimethylcarbamoyl)-N-(methylcarbamoyloxy)thioformimidate(oxamyl

S-methyl-1-carbamoyl-N-(methylcarbamoyloxy)thioformimidate

N-isopropylphosphoramidic acid,O-ethyl-O'-[4-(methylthio)-m-tolyl]diester (fenamiphos).

Insecticides

3-hydroxy-N-methylcrotonamide(dimethylphosphate)ester (monocrotophos)

methylcarbamic acid, ester with 2,3-dihydro-2,2-dimethyl-7-benzofuranol(carbofuran)

O-[2,4,5-trichloro-α-(chloromethyl)benzyl]phosphoric acid,O,',O'-dimethyl ester (tetrachlorvinphos)

2-mercaptosuccinic acid, diethyl ester, S-ester with thionophosphoricacid, dimethyl ester (malathion)

phosphorothioic acid, O,O-dimethyl, O-p-nitrophenyl ester (methylparathion)

methylcarbamic acid, ester with α-naphthol (carbaryl)

methyl N-[[(methylamino)carbonyl]oxy]ethanimidothioate (methomyl)

N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine (chlordimeform)

O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidyl)phosphorothioate(diazinon)

octachlorocamphene (toxaphene)

O-ethyl O-p-nitrophenyl phenylphosphonothioate (EPN)

cyano 93-phenoxyphenyl)-methyl 4-chloro-α-(1-methylethyl)benzeneacetate(fenvalerate)

(3-phenoxyphenyl)methyl(±)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate(permethrin)

dimethyl N,N'-[thiobis(N-methylimmo)carbonylox]]-bis[ethanimidothioate](thiodicarb)

phosphoroethiolothionic acid,O-ethyl-O-[4-(methylthio)phenyl]-S-n-propyl ester (sulprofos)

α-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (cypermethrin)

cyano(3-phenoxyphenyl)methyl4-(difluoromethoxy)-α-(methylethyl)benzenacetate (flucythrinate)

O,O-diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate (chlorpyrifos)

O,O-dimethyl-S-[(4-oxo-1,2,3-bensotriazin-3-(4H)-yl)methyl]phosphorodithioate(azinphos-methyl)

5,6-dimethyl-2-dimethylamino-4-pyrimidinyl dimethyl carbamate(pirimicarb)

S-(N-formyl-N-methylcarbamoylmethyl)-O,O-dimethyl phosphorodithioate(formothion)

S-2-(ethylthioethyl)-O,O-dimethyl phosphiorothioate (demeton-S-methyl)

α-cyano-3-phenoxybenzyl cis-3-(2,2-dibromovinyl)2,2-dimethylcyclopropanecarboxylate (deltamethrin)

cyano(3-phenoxyphenyl)methyl ester ofN-(2-chloro-4-trifluoromethylphenyl)alanine (fluvalinate).

Test results indicate that the compounds of the present invention arealso active preemergent or postemergent herbicides or plant growthregulants. Some of them have utility for broad-spectrum pre-and/orpostemergence weed control in areas where complete control of allvegetation is desired, such as around industrial storage areas, parkinglots, drive-in theaters, around billboards, highway and railroadstructures. Other compounds have utility for selective weed control incrops such as rice, wheat, barley, corn, soybeans, sugarbeets andcotton. Some of the compounds are useful as selective herbicides forrice. They may be used either in direct seeded or transplanted rice.Alternatively, the subject compounds are useful to modify plant growth.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as plant growthmodifiers or as herbicides, the crop species involved, the types ofweeds to be controlled, weather and climate, formulations selected, modeof application, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.050 to 20kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for plant growth modificationor for situations where only short-term persistence is required, such asa herbicide for fallow land.

The compounds of the invention may be used in combination with any othercommercial herbicide, non-limiting examples of which are those below:

    ______________________________________                                                    Chemical Name                                                     ______________________________________                                        Common Name                                                                   acifluorfen   5-[2-chloro-4-(trifluoromethyl)-                                              phenoxy]-2-nitrobenzoic acid                                    acrolein      acrolein                                                        alachlor      2-chloro-2',6'-diethyl-N-                                                     (methoxymethyl)-acetanilide                                     ametryn       2-(ethylamino)-4-(isopropylamino)-6-                                          methylthio- .sub.- s-triazine                                   amitrole      3-amino- .sub.- s-triazole                                      AMS           ammonium sulfamate                                              asulam        methyl sulfanilylcarbamate                                      atrazine      2-chloro-4-(ethylamino)-6-                                                    (isopropylamino)- .sub.- s-triazine                             barban        4-chloro-2-butynyl  .sub.-- m-                                                chlorocarbanilate                                               benefin       N-butyl-N-ethyl-α,α,α-trifluoro-2,6-                        dinitro- -p-toluidine                                           bensulide     0,0-diisopropyl phosphorodithioate                                            S-ester with N-(2-mercaptoethyl)-                                             benzenesulfonamide                                              bentazon      3-isopropyl-1H-2,1,3-                                                         benzothiadiazin-4(3H)-one 2,2-                                                dioxide                                                         benzipram     3,5-dimethyl-N-(1-methylethyl)-N-                                             (phenylmethyl)benzamide                                         benzoylprop   N-benzoyl-N-(3,4-dichlorophenyl)-DL-                                          alaine                                                          bifenox       methyl 5-(2,4-dichlorophenoxy)-2-                                             nitrobenzoate                                                   bromacil      5-bromo-3-sec-butyl-6-methyluracil                              bromoxynil    3,5-dibromo-4-hydroxybenzonitrile                               butachlor     N-(butoxymethyl)-2-chloro-2',6'-                                              diethylacetanilide                                              butam         2,2-dimethyl-N-(1-methylethyl)-N-                                             (phenylmethyl)propanamide                                       buthidazole   3-[5-(1,1-dimethylethyl)-1,3,4-                                               thiadiazol-2-yl]-4-hydroxy-1-                                                 methyl-2-imidazolidinone                                        butralin      4-(1,1-dimethylethyl)-N-(1-methyl-                                            propyl)-2,6-dinitrobenzenamine                                  butylate      S-ethyl-diisobutylthiocarbamate                                 cacodylic acid                                                                              hydroxydimethylarsine oxide                                     carbetamide   D-N-ethyllactamide carbanilate                                                (ester)                                                         CDAA          N-N-diallyl-2-chloroacetamide                                   CDEC          2-chloroallyl diethyldithiocarbamate                            chlorbromuron 3-(4-bromo-3-chlorophenyl)-1-                                                 methoxy-1-methylurea                                            chloroxuron   3-[ -p-( -p-chlorophenoxy)phenyl] 9 -1,1-                                     dimethylurea                                                    chlorpropham  isoproyl  .sub.-- m-chlorocarbanilate                           chlorsulfuron 2-chloro-N[(4-methoxy-6-methyl-                                               1,3,5-triazin-2-yl)amino-                                                     carbonyl]benzene-sulfonamide                                    chlortoluron  N'-(3-chloro-4-methylphenyl-N',N'-                                            dimehylurea                                                     cisanilide    cis-2,5-dimethyl-N-phenyl-1-                                                  pyrrolidine-carboxamide                                         CMA           calcium methanearsonate                                         cyanazine     2-[[4-chloro-6-(ethylamino)- .sub.- s-                                        triazin-2-yl]amino]-2-                                                        methylpropionitrile                                             cycloate      S-ethyl N-ethylthiocyclohexane-                                               carbamate                                                       cycluron      3-cyclooctyl-1,1-dimethylurea                                   cyperquat     1-methyl-4-phenylpyrridinium                                    cyprazine     2-chloro-4-(cyclopropylamino)-6-                                              (isopropylamino)- .sub.- s-triazine                             cyprazole     N-[5-(2-chloro-1,1-dimethylethyl)-                                            1,3,4-thiadiazol-2-yl]                                                        cyclopropanecarboxamide                                         cypromid      3',4'-dichlorocyclopropanecar-                                                boxanilide                                                      dalapon       2,2-dichloropropionic acid                                      dazomet       tetrahydro-3,5-dimethyl-2H-1,3,5-                                             thiadiazine-2-thione                                            DCPA          dimethyl tetrachloroterephthalate                               desmetryn     2-(isopropylamino)-4-(methylamino)-                                           6-methylthio)- .sub.- s-triazine                                diallate      S-(2,3-dichloroallyl)diisopropyl-                                             thiocarbamate                                                   dicamba       3,6-dichloro-o-anisic acid                                      dichlobenil   2,6-dichlorobenzonitrile                                        dichlorprop   2-(2,4-dichlorophenoxy)propionic                                              acid                                                            diclofop      2-[4-(2,4-dichlorophenoxy)phenoxyl]-                                          propanoic acid                                                  diethatyl     N-(chloroacetyl)-N-(2,6-                                                      diethylphenyl)-glycine                                          difenzoquat   1,2-dimethyl-3,5-diphenyl-1H-                                                 pyrazolium                                                      dinitramine   N.sup.4,N.sup.4 -diethyl-α,α,α-trifluoro-3                  ,5-                                                                           dinitrotoluene-2,4-diamine                                      dinoseb       2-sec-butyl-4,6-dinitrophenol                                   diphenamide   N,N-dimethyl-2,2-diphenylacetamide                              dipropetryn   2-(ethylthio)-4,6-bis(isopropyl-                                              amino)- .sub.- s-triazine                                       diquat        6,7-dihydrodipyrido[1,2-α:2',1'-c]-                                     pyrazinediium ion                                               diuron        3-(3,4-dichlorophenyl)-1,1-                                                   dimethylurea                                                    DSMA          disodium methanearsonate                                        endothall     7-oxabicyclo[2.2.1]heptane-2,3-                                               dicarboxylic acid                                               erbon         2-(2,4,5-trichlorophenoxy)ethyl 2.2-                                          dichloropropionate                                              ethafluralin  N-ethyl-N-(2-methyl-2-propenyl)-2,6-                                          dinitro-4-(trifluoromethyl)-                                                  benzenamine                                                     ethofumesate  ( --+)-2-ethoxy-2,3-dihydro-3,3-                                              dimethyl-5-benzofuranyl                                                       methanesulfonate                                                fenac         (2,3,6-trichlorophenyl)acetic acid                              fenoxaprop    ethyl 2-(4-(6-chloro-2-benzoxazolyl-                                          oxy)phenoxy)propanoate                                          fenuron       1,2-dimethyl-3-phenylurea                                       fenuron TCA   1,2-dimethyl-3-phenylurea                                                     mono(trichloracetate)                                           flamprop      N-benzoyl-N-(3-chloro-4-                                                      fluorophenyl)-DL-aniline                                        fluchloralin  N-(2-chloroethyl)-2,6-dinitro-N-                                              propyl-4-(trifluoromethyl)aniline                               fluometuron   1,1-dimethyl-3-(α,α,α-trifluoro- .sub.--                    m-                                                                            tolyl)-urea                                                     fluorodifen    -p-nitrophenyl α,α,α-trifluoro-2-                          nitro- -p-tolyl ether                                           fluridone     1-methyl-3-phenyl-5-[3-(trifluoro-                                            methyl)phenyl]-4-(1H)-pyridinone                                fomesafen     5-(2-chloro-4-trifluoromethyl-                                                phenoxy)-N-methylsulfonyl-2-                                                  nitrobenzamide                                                  fosamine      ethyl hydrogen (aminocarbonyl)-                                               phosphonate                                                     glyphosate    N-(phosphonomehyl)glycine                                       hexaflurate   potasium hexafluoroarsenate                                     hexazinone    3-cyclohexyl-6-(dimethylamino)-1-                                             methyl-1,3,5-triazine-2,4(1H, 3H)-                                            dione                                                           imazaquin     2-(4,5-dihydro-4-methyl-4-(1-methyl-                                          ethyl)-5-oxo-1H-imidazol-2-yl)-3-                                             quinolinecarboxylic acid                                        ioxynil       4-hydroxy-3,5-diiodobenzonitrile                                isopropalin   2,6-dinitro-N,N-dipropylcumidine                                karbutilate   tert-butylcarbamic acid ester with                                            3-( .sub.-- m-hydroxyphenyl)-1,1-                                             dimethylurea                                                    lactofen      1'-(carboethoxy)ethyl-5-(2-chloro-4-                                          (trifluoromethyl)phenoxy)-2-                                                  nitrobenzoate                                                   lenacil       3-cyclohexyl-6,7-dihydro-1H-                                                  cyclopentapyrimidine-2,4(3H,5H)-                                              dione                                                           linuron       3-(3,4-dichlorophenyl)-1-methoxy-1-                                           methylurea                                                      MAA           methanearsonic acid                                             MAMA          monoammonium methanearsonate                                    MCPA          [(4-chloro- -o-tolyl)oxy]acetic acid                            MCPB          4-[(4-chloro- -o-tolyl)oxy]butyric                                            acid                                                            mecoprop      2-[(4-chloro- -o-tolyl)oxy]propionic                                          acid                                                            mefluidide    N-[(2,4-dimethyl-5-                                                           [[(trifluoromethyl)-                                                          sulfonyl]amino]phenyl]acetamide                                 methalpropalin                                                                              N-(2-methyl-2-propenyl)-2.6-dinitro-                                          N-propyl-4-(trifluoromethyl)-                                                 benzenamide                                                     methabenzthiazuron                                                                          1,3-dimethyl-3-(2-benzothiazolyl)                                             urea                                                            metham        sodium methyldithiocarbamate                                    methazole     2-(3,4-dichlorophenyl)-4-methyl-                                              1,2,4-oxadiazolidine-3,5-dione                                  methoxuron    N'-(3-chloro-4-methoxyphenyl)N,N-                                             dimethylurea                                                    metolachlor   2-chloro-N-(2-ethyl-6-methylphenyl)-                                          N-(2-methoxy-1-methylethyl)-                                                  acetamide                                                       metribuzin    4-amino-6-tert-butyl-3-(methylthio)-                                          as-triazine-5(4H)-one                                           metsulfuron methyl                                                                          2-[[(4-methoxy-6-methyl-1,3,5-                                                triazine-2-yl)aminocarbonyl]amino-                                            sulfonyl]benzoic acid, methyl                                                 ester                                                           molinate      S-ethyl hexahydro-1H-azepine-1-                                               carbothioate                                                    monolinuron   3-( -p-chlorophenyl)-1-methoxy-1-                                             methylurea                                                      monuron       3-( -p-chlorophenyl)-1,1-dimethylurea                           monuron TCA   3-( -p-chlorophenyl)-1,1-dimethylurea                                         mono(trichloroacetate)                                          MSMA          monosodium methanearsonate                                      napropamide   2-(α-naphthoxy)-N,N-                                                    diethylpropionamide                                             naptalam      N-1-naphthylphthalamic acid                                     neburon       1-butyl-3-(3,4-dichlorophenyl)-1-                                             methylurea                                                      nitralin      4-(methylsulfonyl)-2,6-dinitro-N,N-                                           dipropylaniline                                                 nitrofen      2,4-dichlorophenyl  -p-nitrophenyl                                            ether                                                           nitrofluorofen                                                                              2-chloro-1-(4-nitrophenoxy)-4-                                                (trifluoromethyl)benzene                                        norea         3-(hexahydro-4.7-methanoindan-5-yl)-                                          1.1-dimethylurea                                                norflurazon   4-chloro-5-(methylamino)-2-(α,α,α-                          trifluoro- .sub.-- m-tolyl)-3(2H)-                                            pyridazinone                                                    oryzalin      3,4-dinito-N,N-dipropylsulfanilamide                            oxadiazon     2-tert-butyl-4-(2,4-dichloro-5-                                               isopropoxyphenyl)Δ.sup.2 -1,3,4-                                        oxadiazolin-5-one                                               oxyfluorfen   2-chloro-1-(3-ethoxy-4-nitro-                                                 phenoxy)-4-(trifluoro-                                                        methyl)benzene                                                  paraquat      1,1'-dimethyl-4,4'-bipyridinium ion                             PBA           chlorinated benzoic acid                                        pendimethalin N-(1-ethylpropyl)-3,4-dimethyl-2,6-                                           dinitrobenzenamine                                              perfluidone   1,1,1-trifluoro-N-[2-methyl-4-                                                (phenylsulfonyl)phenyl]methane-                                               sulfonamide                                                     picloram      4-amino-3,5,6-trichloropicolinic                                              acid                                                            procyazine    2-[[4-chloro-6-(cyclopropylamino)-                                            1,3,5-triazine-2-yl]amino]-2-                                                 methylpropanenitrile                                            profluralin   N-(cyclopropylmethyl)-α,α,α-                                trifluoro-2,6-dinitro-N-propyl- -p-                                           toluidine                                                       prometon      2,4-bis(isopropylamino)-6-methoxy- .sub.- s-                                  triazine                                                        prometryn     2,4-bis(isopropylamino)-6-                                                    (methylthio)- .sub.- s-triazine                                 pronamide     3,5-dichloro N-(1,1-dimethyl-2-                                               propyn-yl)enzamide                                              propachlor    2-chloro-N-isopropylacetanilide                                 propanil      3',4'-dichloroprionalide                                        propazine     2-chloro-4,6-bis(isopropylamino)- .sub.- s-                                   triazine                                                        propham       isopropyl carbanilate                                           prosulfalin   N-[[4-(dipropylamino)-3,5-                                                    dinitrophenyl]sulfonyl]-S,S-                                                  dimethylsulfilimine                                             prynachlor    2-chloro-N-(1-methyl-2-                                                       propynyl)acetanilide                                            quinofop ethyl                                                                              2-[4-(6-chloroquinoxalin-2-yloxy)-                                            phenoxypropanoic acid, ethyl ester                              secbumeton    N-ethyl-6-methoxy-N'(1-                                                       methylpropyl)-1,3,5-triazine-2,4-                                             diamine                                                         sethoxydim    2-[1-(ethoxyimino)butyl]-5-[2-                                                (ethylthio)propyl]-3-hydroxy-2-                                               cyclohexene-1-one                                               siduron       1-(2-methylcyclohexyl)-3-phenylurea                             simazine      2-chloro-4,6-bis(ethylamino)- .sub.- s-                                       triazine                                                        simetryn      2,4-bis(ethylamino)-6-(methylthio)-                                            .sub.- s-triazine                                              supriox       2-[ 1-(2,5-dimethylphenyl)-                                                   ethylsulfonyl]-pyridine-N-oxide                                 TCA           trichloroacetic acid                                            tebuthiuron   N-[5-(1,1-dimethylethyl)-1,3,4-                                               thiadiazol-2-yl]-N,N'-dimethylurea                              terbacil      3-tert-butyl-5-chloro-6-methyluracil                            terbuchlor    N-(butoxymethyl)-2-chloro-N-[2-(1.1-                                          dimethylethyl)-6-methylphenyl]-                                               aceamide                                                        terbuthylazine                                                                              2-(tert-butylamino)-4-chloro-6-                                               (ethylamino)- .sub.- s-triazine                                 terbutol      2,6-di-tert-butyl- -p-tolyl                                                   methylcarbamate                                                 terbutryn     2-(tert-butylamino)-4-(ethylamino)-                                           6-(methylthio)- .sub.- s-triazine                               tetrafluron   N,N-dimethyl-N'-[3-(1,1,2,2-                                                  tetrafluoroethoxy)phenyl]urea                                   thiobencarb   S-[(4-chlorophenyl)methyl]                                                    diethylcarbamothioate                                           triallate     S-(2,3,3-trichloroallyl)-                                                     diisopropylthiocarbamate                                        trifluralin   α,α,α-tifluoro-2,6-dinitro-N,N-                             propyl- -p-toluidine                                            trimeturon    1-( -p-chlorophenyl)-2,3,3-                                                   trimethylpseudourea                                             vernolate     S-propyl dipropylthiocarbamae ethyl                                           5-[2-chloro-4-(trifluoromethyl)-                                              phenoxy]-2-nitrobenzoic acid                                    2,3,6-TBA     2,3,6-trichlorobenzoic acid                                     2,4-D         (2,4-dichlorophenoxy)acetic acid                                2,4-DB        4-(2,4-dichlorophenoxy)butyric acid                             2,4-DEP       tris[2-(2,4-dichlorophenoxy)ethyl]                                            phosphite                                                       Trade Name or                                                                 Code Number                                                                   "Cinch"       exo-1-methyl-4-(1-methylethyl)-2-[2-                                          methylphenyl)methoxy]7-                                                       oxabicyclo[2.2.1]heptane                                        AC 263,499    2-[4,5-dihydro-4-methyl-4-(1-methyl-                                          ethyl)-5-oxo-1H-imidazol-2-yl]-5-                                             ethyl-3-pyridinecarboxylic acid                                 Harmony.sup. ™                                                                           3-[[(4-methoxy-6-methyl-1,3,5-                                                triazin-2-yl)aminocarbonyl]amino-                                             sulfonyl]-2-thiophenecarboxylic                                               acid, methyl eser                                               PPG-1013      5-(2-chloro-4-(trifluoromethyl)-                                              phenoxy)propanoic acid, methyl                                                ester                                                           FMC 57020     2-(2'-chlorophenyl)methyl-4,4-                                                dimethyl-3-isoxazolidinone                                      AC 222,293    6-(4-isopropyl-4-methyl-5-oxo-2-                                              imidazolin-2-yl)- .sub.-- m-toluic                                            acid, methyl ester and 6-(4-                                                  isopropyl-4-methyl-5-oxo-2-                                                   imidazolin-2-yl- -p-toluic acid,                                              methyl ester                                                    ______________________________________                                    

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

This invention is further illustrated by the following examples.

EXAMPLE A

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the point ofrun-off on apple seedings. The following day plants were inoculated witha spore suspension of Venturia inaequalis, the causal agent of applescab, and incubated in a saturated humidity chamber at 20° C. for 24hours and then in a growth chamber at 220° C. for 11 days, when diseaseratings were made.

EXAMPLE B

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the point ofrun-off on peanut seedlings. The following day plants were inoculatedwith a spore suspension of Cercosporidium personatum, the casual agentof Peanut Late Leafspot, and incubated in a saturated humidity chamberat 22° C. for 24 hours, then in a high humidity chamber at 27° C. for 7days, and then in a growth chamber at 29° C. for 7 days, when diseaseratings were made.

EXAMPLE C

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the pont ofrun-off on broad bean seedlings. The following day plants wereinoculated with a spore suspension of Botrytis cinerea, the causal agentof bean grey mod, and incubated in a saturated humidity chamber at 20°C. for 24 hours when disease ratings were made.

EXAMPLE D

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the point ofrun-off on what seedlings. The following day plants were inoculated witha spore dust of Erysiphe graminis f. sp. tritici, the causal agent ofwheat powdery mildew and incubated in a growth chamber at 20° C. for 6days, when disease ratings were made.

EXAMPLE E

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the point ofrun-off on rice seedlings. The following day plants were inoculated witha spore suspension of Pyricularia orysae, the causal agent of riceblast, and incubated in a saturated humidity chamber at 27° C. for 24hours and then in a growth chamber at 29° C. for 4 days, when diseaseratings were made.

EXAMPLE F

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the point ofrun-off on rice seedlings. The following day plants were inoculated witha spore suspension of Rhizoctonia solani, the causal agent of ricesheath blight, and incubated in a saturated humidity chamber at 27° C.for 48 hours and then in a growth chamber at 29° C. for 4 days, whendisease ratings were made.

EXAMPLE G

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the point ofrun-off on wheat seedlings. The following day plants were inoculatedwith a spore suspension of Puccinia recondita, the causal agent of wheatleaf rust, and incubated in a saturated humidity chamber at 20° C. for24 hours and then in a growth chamber at 20° C. for 8 days, when diseaseratings were made.

EXAMPLE H

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the point ofrun-off on tomato seedlings. The following day plants were inoculatedwith a spore suspension of Phytophthora infestans, the causal agent oftomato late blight, and incubated in a saturated humidity chamber at 20°C. for 24 hours and then in a growth chamber at 20° C. for 5 days, whendisease ratings were made.

EXAMPLE I

The test compounds were dissolved in acetone in an amount equal to 6% ofthe final volume and then suspended at a concentration of 100 or 20 ppmin purified water containing 250 ppm of the surfactant TREM 014(polyhydric alcohol esters). This suspension was sprayed to the point ofrun-off on grape seedlings. The following day plants were inoculatedwith a spore suspension of Plasmorpara viticola, the causal agent ofgrade downy mildew, and incubated in a saturated humidity chamber at 20°C. for 24 hours, then in a growth chamber at 20° C. for 7 days and thenheld in a saturated humidity chamber at 20° C. for 24 hours, whendisease ratings were made.

EXAMPLE J

The test compounds were dissolved in acetone so that 1 ml of solutionyielded a concentration of 0.5 kilogram/hectare when added to cucumberseeds and soil in pots. Seeds and soil were then inoculated with amixture of sand, cereal and mycelium of the fungus Pythiumaphanadermatum, causal agent of cucumber damping off, and incubated in agrowth chamber at 30° C. for 14 days. Disease ratings were then made.

EXAMPLE K

The test compounds were dissolved in acetone so that 1 ml of solutionyielded a concentration of 0.5 kilogram/hectare when added to cottonseeds and soil in pots. Seeds and soil were then inoculated with amixture of sand, cereal and mycelium of the fungus Rhizoctonia solani,causal agent of cotton blight, and incubated in a growth chamber at 30°C. for 14 days. Disease ratings were then made.

EXAMPLE L

The test compounds were dissolved in acetone so that 1 ml of solutionyielded a concentration of 0.5 kilogram/hectare when added to cucumberseeds and soil in pots. Seeds and soil were then inoculated with amixture of sand, cereal and mycelium of the fungus Fusarium oxysporum f.sp. cucumerinum, causal agent of cucumber wilt, and incubated in agrowth chamber at 30° C. for 14 days. Disease ratings were then made.

EXAMPLE M

The test compounds were dissolved in acetone so that 1 ml of solutionyielded a concentration of 0.5 kilogram/hectare when added to lima beanseeds and soil in pots. Seeds and soil were then inoculated with amixture of sand, cereal and mycelium of the fungus Sclerotium rolfsii,causal agent of southern blight, an incubated in a growth chamber at 30°C. for 14 days. Disease ratings were then made.

Results for Examples A-M are given in Table 7. In this table, a ratingof 100 indicates 100% disease control and a rating of 0 indicates nodisease control relative to the controls. A--entry indicates that notest was performed with the specified compound. A P entry indicates thatdisease control was not measured due to phytoxicity.

                                      TABLE 7                                     __________________________________________________________________________    Ex. Rate                                                                              Ex.                                                                              Ex.                                                                              Ex.                                                                              Ex.                                                                              Ex.                                                                              Ex.                                                                              Ex.                                                                              Ex.                                                                              Ex.                                                                              Rate Ex.                                                                              Ex.                                                                              Ex.                                                                              Ex.                          No. (PPM)                                                                             A  B  C  D  E  F  G  H  I  (kg/ha)                                                                            J  K  L  M                            __________________________________________________________________________    1   100 62 100                                                                              81 98 90 97 100                                                                              0  12 5    0  P  0  P                            2   100 62 100                                                                              93 98 95 100                                                                              100                                                                              0  99 5    0  P  0  P                            3   100 100                                                                              100                                                                              93 93 5  93 100                                                                              0  0  5    0  0  P  P                            4   100 100                                                                              100                                                                              88 100                                                                              96 100                                                                              100                                                                              0  81 5    0  0  P  0                            6   100 0  82 84 98 0  0  96 23 0  5    0  0  P  0                            10  100 0  76 52 63 0  17 64 0  0  5    0  0  0  0                            15  100 100                                                                              100                                                                              99 100                                                                              1  93 100                                                                              26 0  5    0  P  0  P                            16  100 -- -- 46 -- 0  0  -- 0  23 5    0  0  P  0                                20  74 99 27 67 0  0  100                                                                              -- --                                            17  100 -- -- 89 -- 0  81 -- 0  42 5    0  0  P  0                                20  80 100                                                                              57 95 0  0  100                                                                              -- --                                            25  100 100                                                                              100                                                                              96 91 31 48 97 0  0  5    0  P  P  35                           26  100 100                                                                              100                                                                              96 86 31 61 97 23 86 5    0  25 25 35                           27  100 62 100                                                                              88 98 95 100                                                                              100                                                                              24 84 5    0  0  0  0                            28  100 89 100                                                                              88 98 81 100                                                                              100                                                                              0  6  5    0  0  0  0                            32  100 100                                                                              100                                                                              98 95 97 33 100                                                                              0  98 5    0  0  P  P                            33  100 -- -- 56 -- 0  60 -- 0  24 5    0  0  0  0                                20  47 99 37 89 0  29 100                                                                              -- --                                            34  100 69 100                                                                              94 60 86 16 66 0  0  5    0  0  0  0                            35  100 100                                                                              100                                                                              96 100                                                                              0  100                                                                              96 0  26 5    0  0  0  0                            39  100 89 97 96 98 7  100                                                                              100                                                                              0  81 5    0  0  0  0                            40  100 19 100                                                                              80 91 7  61 96 0  0  5    0  0  0  0                            41  100 100                                                                              100                                                                              96 98 7  97 100                                                                              0  100                                                                              5    0  0  0  0                            42  100 -- -- 100                                                                              100                                                                              31 41 -- 0  23 5    -- -- -- --                               20  29 100                                                                              38 98 15 0  100                                                                              -- --                                            47  100 -- -- 89 -- 31 47 -- 0  25 5    -- -- -- --                               20  93 100                                                                              26 98 15 0  100                                                                              -- --                                            49  100 89 100                                                                              62 100                                                                              76 96 100                                                                              0  0  5    0  P  0  P                            50  100 100                                                                              100                                                                              98 95 86 93 100                                                                              0  46 5    0  P  0  P                            51  100 100                                                                              100                                                                              96 100                                                                              0  100                                                                              100                                                                              0  0  5    P  P  P  P                            52  100 100                                                                              100                                                                              95 94 93 81 100                                                                              0  0  5    0  P  0  0                            65  100 34 96 94 85 30 62 100                                                                              0  0  5    0  0  0  0                            67  100 -- -- 75 -- 0  68 -- 2  1  5    0  0  0  0                                20  58 99 60 85 0  35 89 -- --                                            94  100 86 61 96 98 78 36 100                                                                              0  0  5    0  0  P  P                            99  100 100                                                                              100                                                                              89 83 98 61 100                                                                              0  83 5    0  0  P  P                            100 100 100                                                                              100                                                                              96 83 95 80 100                                                                              0  83 5    P  0  P  0                            101 100 100                                                                              100                                                                              94 83 0  80 100                                                                              0  100                                                                              5    0  0  P  0                            163 100 -- -- 95 -- 5  0  -- 0  0  5    -- -- -- --                               20  0  81 58 23 5  0  99 -- --                                            164 100 -- -- 84 -- 15 0  -- 8  0  5    -- -- -- --                               20  82 100                                                                              57 88 5  0  100                                                                              -- --                                            170 100 -- -- 20 -- 10 0  -- 0  0  5    -- -- -- --                               20  19 69 32 95 0  0  100                                                                              -- --                                            177 100 -- -- 26 -- 10 0  -- 0  0  5    -- -- -- --                               20  82 26 50 46 0  0  100                                                                              -- --                                            208 100 84 37 83 76 4  61 97 0  74 5    0  0  0  0                            291 100 -- -- 81 -- 1  0  -- 24 78 5    -- -- -- --                               20  32 26 6  83 1  0  73 -- --                                            359 100 72 100                                                                              83 95 88 62 100                                                                              0  0  5    0  0  0  0                            360 100 88 100                                                                              71 86 74 49 93 0  0  5    0  0  0  0                            361 100 -- -- 46 -- 1  0  -- 27 9  5    -- -- -- --                               20  43 26 29 33 1  0  100                                                                              -- --                                            363 100 0  49 92 28 0  0  38 0  0  5    0  0  0  0                            447 100 -- 0  24 46 46 0  30 0  24 5    0  0  0  0                            448 100 -- 0  54 -- 0  42 16 0  0  5    -- -- -- --                           449 100 71 0  24 0  76 13 30 0  51 5    0  0  0  0                            450 100 -- 0  54 11 46 34 30 0  51 5    0  0  0  0                            451 100 16 100                                                                              72 0  0  0  0  0  0  5    0  0  0  0                            452 100 36 0  54 46 0  67 30 0  0  5    0  0  0  0                            453 100 55 32 75 94 0  0  100                                                                              0  0  5    0  0  0  0                            454 100 0  0  0  22 0  0  0  0  0  5    -- -- -- --                           455 100 64 65 0  12 0  0  43 0  0  5    0  0  0  0                            456 100 82 0  58 53 98 0  96 9  0  5    0  0  0  0                            477 100 95 100                                                                              76 100                                                                              48 48 100                                                                              0  0  5    P  P  P  P                            594 100 86 100                                                                              93 77 2  -- 100                                                                              0  79 5    0  60 100                                                                              50                           596 100 -- -- 89 -- 0  0  -- 0  25 5    -- -- -- --                               20  91 95 35 94 0  0  100                                                                              -- --                                            603 100 44 97 91 69 0  -- 95 0  0  5    0  0  0  0                            605 100 70 99 32 81 0  -- 100                                                                              0  0  5    0  0  0  0                            608 100 87 100                                                                              98 98 4  81 100                                                                              0  0  5    0  0  P  P                            618 100 100                                                                              100                                                                              98 89 0  -- 100                                                                              0  0  5    0  80 80 P                            620 100 100                                                                              100                                                                              96 98 51 100                                                                              100                                                                              0  0  5    0  0  P  0                            622 100 100                                                                              100                                                                              84 99 0  100                                                                              100                                                                              0  26 5    0  0  P  0                            627 100 -- -- 38 -- 0  14 -- 0  61 5    -- -- -- --                               20  31 70 19 81 0  0  99 -- --                                            644 100 100                                                                              100                                                                              94 100                                                                              100                                                                              100                                                                              100                                                                              23 0  5    0  0  P  P                            646 100 100                                                                              100                                                                              95 98 97 61 100                                                                              0  99 5    100                                                                              0  0  0                            651 100 -- -- 42 -- 0  62 -- 0  46 5    0  0  0  0                                20  67 0  7  67 0  0  100                                                                              -- --                                            656 100 93 100                                                                              88 97 0  50 100                                                                              0  20 5    0  P  P  P                            657 100 62 100                                                                              81 98 49 97 100                                                                              24 37 5    0  0  0  0                            661 100 -- -- 56 -- 0  70 -- 5  85 5    -- -- -- --                               20  81 79 61 62 0  10 100                                                                              -- --                                            663 100 42 100                                                                              95 99 57 36 100                                                                              0  39 5    -- -- -- --                           667 100 -- -- 4  -- 0  0  -- 0  10 5    0  0  0  0                                20  13 14 7  39 0  0  0  -- --                                            668 100 -- -- 76 -- 1  0  -- 22 31 5    -- -- -- --                               20  65 17 31 31 1  0  100                                                                              -- --                                            669 100 100                                                                              100                                                                              90 100                                                                              96 100                                                                              100                                                                              0  0  5    0  0  P  0                            671 100 100                                                                              100                                                                              92 94 84 100                                                                              100                                                                              0  84 5    0  P  P  0                            675 100 -- -- 30 -- 0  62 -- 0  69 5    -- -- -- --                               20  40 0  42 44 0  0  16 -- --                                            685 100 -- -- 0  -- 0  29 -- -- -- 5    -- -- -- --                               20  57 66 28 67 -- 15 100                                                                              -- --                                            721 100 73 89 95 94 18 100                                                                              100                                                                              0  0  5    P  P  P  P                            724 100 100                                                                              100                                                                              95 100                                                                              63 100                                                                              100                                                                              0  0  5    0  P  P  P                            726 100 -- -- -- -- 0  0  -- 0  38 5    0  20 0  0                                20  75 0  23 81 0  0  100                                                                              -- --                                            815 100 40 98 0  62 2  -- 97 0  65 5    0  0  0  0                            905 100 -- -- 19 -- 0  37 -- 0  87 5    0  0  0  0                                20  7  0  15 47 0  0  16 -- --                                            1276                                                                              100 100                                                                              -- 96 100                                                                              1  97 100                                                                              0  0  5    0  P  0  P                                20  93 100                                                                              86 100                                                                              1  52 100                                                                              -- --                                            1276a                                                                             100 -- -- 53 -- 1  0  -- 16 22 5    -- -- -- --                               20  42 26 33 88 1  0  100                                                                              -- --                                            1277                                                                              100 9  65 0  0  0  0  39 0  25 5    0  0  0  0                            1277a                                                                             100 -- -- 36 -- 1  52 -- 8  31 5    -- -- -- --                               20  58 74 24 95 1  0  100                                                                              -- --                                            1278                                                                              100 100                                                                              100                                                                              87 85 17 36 100                                                                              0  16 5    0  0  0  0                            1300                                                                              100 100                                                                              100                                                                              93 92 58 81 100                                                                              0  0  5    0  0  0  0                            1304                                                                              100 100                                                                              100                                                                              97 100                                                                              78 88 100                                                                              0  18 5    0  0  0  0                            1377                                                                              100 100                                                                              100                                                                              96 92 58 100                                                                              100                                                                              0  44 5    0  P  0  P                            1381                                                                              100 100                                                                              100                                                                              97 98 51 73 100                                                                              0  78 5    0  50 0  0                            1451                                                                              100 86 84 48 77 2  -- 93 0  79 5    0  0  0  0                            1459                                                                              100 72 70 65 31 17 0  65 0  74 5    0  0  0  0                            1468                                                                              100 40 0  0  77 2  -- 93 0  46 5    0  60 0  0                            1469                                                                              100 68 84 81 77 2  -- 100                                                                              24 89 5    0  80 70 0                            1527                                                                              100 0  100                                                                              93 100                                                                              -- 35 100                                                                              0  0  5    0  P  0  P                            __________________________________________________________________________

TEST A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), giant foxtail (Setaria faberii), wild oats (Avena fatua),cheatgrass (Bromus secalinus), velvetleaf (Abutilon theophrasti),morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum),sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley andpurple nutsedge (Cyperus rotundus) tubers were planted and treatedpreemergence with the test chemicals dissolved in a non-phytotoxicsolvent. At the same time, these crop and weed species were treated witha soil/foliage application. At the time of treatment, the plants rangedin height from 2 to 18 cm. Treated plants and controls were maintainedin a greenhouse for sixteen days, after which all species were comparedto controls and visually rated for response to treatment. The ratings,summarized in Table A, are based on a numerical scale extending from0=no injury, to 10=complete kill. The accompanying descriptive symbolshave the following meanings:

C=chlorosis/necrosis;

B=burn;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation;

X=axillary simultation;

S=albinism; and

Y=abscised buds or flowers.

    TABLE A      POSTEMERGENCE CMPD 52 CMPD 52 (salt) CMPD 56 CMPD 56 (salt) CMPD 57     CMPD 58 CMPD 59 CMPD 61 CMPD 66 CMPD 67 CMPD 99       RATE = KG/HA 0.1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER     COTTON 2H 2H 0 7F,9G 4H 10P,9G 10P,9G 0 2H 10P,9G 10P,9G 5H CULT     MORNINGLRY 2C,4H 3C,6H 0 4C,9G 3C,7G 5C,9G 2C,3G 3C,5H  5C,9G 2C,2G     2C,4H COCKLEBUR 0 2C 0 3H,8G 2C 1H 2C,8H 0 1C 2C,5H 2C,5G 4C,7H PURPLE     NUTSEDGE 0 --  0 0 5G 0 0 0 0 0 0 LARGE CRABGRASS 0 3C,6G 0 4G 0 9C     2C,8H 0 0 0 4G 9G BARNYARDGRASS 0 0 0 5G 0 7H 0 0 0 0 0 0 WILD OATS 0     2C,4G 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 0 0 0 0 G4646 CORN 0     0 0 0 0 0 0 0 0 0 0 0 WILLMS SOYBEANS 0 1C 0 3C,8G 1C 4C,9G 4C,9G 1C,1H     3H 3C,4H 1C,4H 3C,5H RICE DRY SEEDED 0 1C 0 0 0 0 0 0 0 0 0 0 G522     SORGHUM 0 0 0 0 0 0 0 0 0 0 0 0 CHEAT GRASS   0 0  0 0   0 0 0 USN11     SUGARBEET 0 4G 0 5H,5I 2H 4H,5I 3H,7G 4H 3H 8H,5I 7H,5I 7H VELVETLEAF 3G     2C,5G 0 7G 2G 4C,9G 2C,8G 0 3C,5G 3G 2C,5G 8G GIANT FOXTAIL 0 2C,5G 0 0     0 9G 0 0 0 0 0 0 KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME 0 0     0   0 0        CMPD 101 CMPD 106 CMPD 107 CMPD 108 CMPD 208 CMPD 594 CMPD 594 CMPD     596 CMPD 598 CMPD 603 CMPD 605 CMPD 611       RATE = KG/HA 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER     COTTON 9G,10P 4G 10P,8G 6H 0 4G 3G 0 8G 0 0 7G CULT MORNINGLRY 5C,9H     2C,8G 5C,9G 3C,6G 2C,5H 6G 2C,2H 2C 0 3B 2B 0 COCKLEBUR 3C,6H 2C,2H     3C,5G 2C,2H 2C 2C 0 1C 2C 1B 1B 1H PURPLE NUTSEDGE 0 5G 0 0 5G  0 0 3G 0     0 0 LARGE CRABGRASS 7G 2G 0 0 0 2G 2G 0 2G 0 0 5G BARNYARDGRASS 0 5H 7H     0 0 0 0 0 0 0 0 2C WILD OATS 0 0 0 0 0 0 0 0 2G 0 0 0 ERA WHEAT 0 0 0 0     0 0 0 0 3G 0 0 0 G4646 CORN 0 0 0 0 0 0 2G 0 0 0 0 0 WILLMS SOYBEANS     2C,4H 2C,5G 5C,9G 2C,7G 2C,2H 2B,3H 2C,3H 2C 2C,2H 0 1C 2C,4H RICE DRY     SEEDED 0 0 2C,5G 0 0 3G 0 0 0 0 0 0 G522 SORGHUM 0 0 0 0 0 0 0 0 0 0 0 0     CHEAT GRASS 0 0   0 0 0 0 0 0 0 0 USN11 SUGARBEET 6H 5G 0 3C,6G 6H 0 3G     1H 4G,5I 0 0 0 VELVETLEAF 9H 3C,7G 3C,6G 2C,5G 8G 2C 0 1C 0 1B 0 0 GIANT     FOXTAIL 0 0 0 0 0 0 2G 0 3G 0 0 0 KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0     DOWNY BROME   0 0       CMPD 618 CMPD 620 CMPD 624 CMPD 627 CMPD 644 CMPD 644 CMPD 646 CMPD     648 CMPD 651 CMPD 653 CMPD 656 CMPD 658       RATE = KG/HA 2 0.4 2 0.4 0.4 2 0.1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER     COTTON 6P,9G 3H 10P,9G 2H,9G 1C  5G 2C,7G 9G,10P 9P,9G 0 10P,9G 7G 0     CULT MORNINGLRY 0 2C,5G 3C,8G 2C,3H 2C,6G 6C,9G 3C,3G 3C,5G 3C,8G 1C 2C     2C 2C,3H 0 COCKLEBUR 1H 2C,2H 3C,9G 2C,5H 2C 5C,8H 0 2C 2C 2C 1C 2C,5G     2C 0 PURPLE NUTSEDGE 0 0 5G 0 0 8G,5X 0 0 0 0 0  2G 0 LARGE CRABGRASS 8G     9G 2C,9G 9C 0 3C,9G 0 0 6G 0 0 5C,9G 2G 0 BARNYARDGRASS 0 2H 3C,9H 6H 0     5C,9H 0 0 0 0 0 0 0 0 WILD OATS 0 0 0 0 0 3C,6G 0 0 0 0 0 0 0 0 ERA     WHEAT 0 0 0 2G 0 4C,8G 0 0 0 0 0 0 0 0 G4646 CORN 0 3C,3H 3C,7H 0 0     3C,6H 0 0 0 0 2G 2G 0 0 WILLMS SOYBEANS 2C,4G 3C,8G 4C,9G 3C,8H 1H 9C     2C,2H 2C,5H 5C,8H 2C 1C 3C,7G 2C 0 RICE DRY SEEDED 0 2C,4G 2C,8G 0 0     3C,8G 0 1C 0 0 0 0 0 0 G522 SORGHUM 0 2C 2C,3H 0 0 3C,9H 0 0 0 0 0 0 0 0     CHEAT GRASS 0 0 8G 0 0 2C,8G   0 0 0 0 0 0 USN11 SUGARBEET 5H 3H 8H     7H,5I 2H 5G,5I 2G 7G 4H 4G,5I 1H 2C,7H 4H 0 VELVETLEAF 2C,7G 3C,5H 2C,9G     1C 0 9G 3G 2C,6G 2C,3G 2C,5G 0 1C  8G GIANT FOXTAIL 8G 2C,7H 9G 2C,9G 0     3C,9G 0 2C,3G 0 0 0 2C,7H 0 0 KLAGES BARLEY 0 0 0 0 0 2C,9G 0 0 0 0 0 0     0 0 DOWNY BROME       0 0        CMPD 659 CMPD 661 CMPD 669 CMPD 673 CMPD 675 CMPD 721 CMPD 724 CMPD     724 CMPD 726 CMPD 753 CMPD 754 CMPD 782       RATE = KG/HA 0.4 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER     COTTON 0 1C,3H 3C,7H 10P,9G 0 5G 6G 10P,9G 4H 10P,9G 2H 10P,9G CULT     MORNINGLRY 3C,6G 1C 6C,9G 2C,1H 1C 3C,6H 3C,5H 5C,9G 3C,7G 4C,9G 5C,9G     5C,9G COCKLEBUR 2C 1C 3C,7G 2C,3H 0 2C 3C,4H 3C,9H 1C,2H 2C,6G 2C,3H 8G     PURPLE NUTSEDGE 0 0 4G 0 0 0 2C,8H 0 0 0 0 0 LARGE CRABGRASS 0 0 2G     3C,3G 0 0 9G 5G 0 4C,9G 0 5C,9G BARNYARDGRASS 0 0 5C,9G 0 0 0 2C,3H 7G 0     5H 0 7H WILD OATS 0 0 2C,4G 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 2G 0 0 0 0     2G 0 0 0 0 G4646 CORN 0 0 0 0 0 0 0 0 2G 0 0 0 WILLMS SOYBEANS 3C 1H     5C,9G 1C,1H 1C 2C 4C,8H 3C,9G 2H 9C 2C,3H 8G RICE DRY SEEDED 0 0 0 0 0 0     5G 0 0 0 0 0 G522 SORGHUM 0 0 2G 0 0 0 0 0 0 2G 0 0 CHEAT GRASS 0 0 3G 0     0 0 0 0 0 0  0 USN11 SUGARBEET 0 4H 5G,5I 8H,5I 1C 3H 7H 3H 3H 8H 7G     7H,5I VELVETLEAF 2C,5G 1C 6G 1C 0 6G 9H 3C,9G 0 3C,8G 3G 8G GIANT     FOXTAIL 0 0 2G 9H 0 0 9G 9G 5G 2C,8G 0 7G KLAGES BARLEY 0 0 2G 0 0 0 0 0     0 0 0 0 DOWNY BROME           0       CMPD 784 CMPD 810 CMPD 811 CMPD 815 CMPD 863 CMPD 879 CMPD 905 CMPD     1276 CMPD 1276 (salt) CMPD 1276A  CMPD 1277       RATE = KG/HA 0.4 0.4 0.4 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER     COTTON 10P,9G 0 10P,9G 9G,10P 2B 2C,6G 0 0 4H 9G,10P 7G 3H,6G CULT     MORNINGLRY 3H 2C,5G 5C,9G 3C,9H 0 1C,2G 1C,2H 2C 2C,4H 2C,3G 1C 2C,3G     COCKLEBUR 2H 8G 3H,8G 2C,4H 0 2C 1C 0 2C 3C 1C 2C,7G PURPLE NUTSEDGE 0     0 0 0 0 0 0 0 0  0 LARGE CRABGRASS 6H 5G 9C 0 1B 0 3G 0 0 0 0 4G     BARNYARDGRASS 0 2G 3C,9G 0 1B 0 0 0 0 0 0 1C WILD OATS 0 0 0 0 0 0 0 0 0     0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 0 0 0 0 G4646 CORN 0 0 0 0 1B 0 0 0 0 0     0 0 WILLMS SOYBEANS 2C,5H 5G 3C,9G 0 2B 2C 2H,5G 0 2C,6H 3C 2H,6G 1C,1H     RICE DRY SEEDED 0 0 0 0 0 0 2G 0 0 0 0 0 G522 SORGHUM 0 0 0 0 0 0 0 0 0     0 2G 0 CHEAT GRASS 0 0 0 0 0 0 0 0 0 0 0 0 USN11 SUGARBEET 7H 4G 6H,5I 0     1B 0 3G 0 2H 0 3H 1H VELVETLEAF 2H 8G 4C,9G 0 2B 2C 2G 0 8G 2C,4G 2C 0     GIANT FOXTAIL 2G 2G 9G 0 1B 0 0 0 0 0 0 3G KLAGES BARLEY 0 0 0 0 0 0 0 0     0 0 0 0 DOWNY BROME       CMPD 1278 CMPD 1279 CMPD 1280 CMPD 1377 CMPD 1381 CMPD 1304 CMPD 1      CMPD 4 CMPD 9 CMPD 11 CMPD 13       RATE = KG/HA 0.4 0.4 0.4 0.4 2 0.4 2 0.4 2 0.4 0.4 0.1 0.4 2 0.4 COKER     COTTON 0 10P,9G 7G 9G,10P 9G,10P 3G 10P,9G 5H 10P,9G 3H 3C,9H 3H 3H     10P,9G 6H CULT MORNINGLRY 1C 5C,9G 2H 2C,6H 4C,9H 3C,5G 2C,8H 3C,7G     2C,7G 1C,1H 4C,8H 3C,4H 3C,6G 4C,9G 4C,8G COCKLEBUR 1C 5H 4H 2C,3H 4C,9H     2C 2C,7H 2C,4G 8H 1C,3G 3C,8H 0 3C,6G 3C,9G 3C,3H PURPLE NUTSEDGE 0 0 0     -- 4G 0 2C,5G 0 8G 0 5G 0 9G 7G 0 LARGE CRABGRASS 4G 3C,5G 9H 0 4C,9G 2G     4C,9G 3C,7G 3C,9G 0 9G 0 3G 9C 0 BARNYARDGRASS 0 2G 5H 2G 5C,9H 2H 9H 5H     9H 0 2C,8H 0 0 5C,9G 0 WILD OATS 0 0 0 0 0 0 2G 0 2G 0 0 0 0 7G 0 ERA     WHEAT 0 0 0 0 0 0 2G 0 4G 0 0 0 0 8G 0 G4646 CORN 0 0 0 0 0 0 3G 0 3G 2G     2G 0 0 7H 0 WILLMS SOYBEANS 0 3C,5G 5C,9G 3C,5H 3C,6H 2C,4G 2C,8G 2C,5G     2C,6G 2C,3H 4C,8G 1C,1H 2C,4H 4C,9G 3C,5G RICE DRY SEEDED 0 0 0 0 0 0 8G     0 7G 0 5G 0 1C 3C,7G 0 G522 SORGHUM 0 0 2G 0 0 0 9H 0 7G 0 5G 0 0 3C,8H     2G CHEAT GRASS 0 0 0 0 2G -- 2G -- 5G 0 5G   7G USN11 SUGARBEET 1H 7H,5I     8H 6H,5I 7H,5I 5G 9H 2H 7H,5I 8G 6H 3G 3G 9H,5I 7G VELVETLEAF 0 3C,7G 7H     2C,3H 3C,7H 0 9G 0 9G 0 2C,8H -- 4G 3C,9G 2C GIANT FOXTAIL 0 0 9H 0     3C,9H 0 9G 0 9H 0 9G 0 2C,2G 9G 3G KLAGES BARLEY 0 0 0 0 0 0 2G 0 3G 0 0     0 0 5G 0 DOWNY BROME      0 -- 0 --   0 0  0       CMPD 15 CMPD 16 CMPD 17 CMPD 18 CMPD 23 CMPD 33 CMPD 34 CMPD 34 CMPD     34 CMPD 35 CMPD 35 (salt)       RATE = KG/HA 0.4  0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2 2 COKER COTTON     7G 8G 3H 7G,5I 2H 10P,9G 10P,8G 8P,8G 4G 10P,9G 10P,9G 10P,9G CULT     MORNINGLRY 2C,4H 4C,9G 3C,4G 2C 2C,3H 2C,5G 3C,10P 5C,9G 0 10P,9G 4C,9G     5C,9G COCKLEBUR 2C 2C,6G 2C,5G 2C,3G 1C,1H 3C,4H 2C,2H 2C,2H 2C,3H 2C,5G     3C,8G 4C,9H PURPLE NUTSEDGE 0 0 0 0 0 0 0 0 0 2G 8G 8G LARGE CRABGRASS 0     8G  3C,7G 3G 5C,9G 3G 0 5G 2C,9G 3C,9G 3C,9G BARNYARDGRASS 3G 0 0 9H 0 0     0 0 5H 2C,8H 4C,9H 5C,9G WILD OATS 0 0 0 0 0 0 0 0 0 0 1C 0 ERA WHEAT 0     0 0 0 0 0 0 0 0 0 0 0 G4646 CORN 0 0 0 0 0 2G 0 0 0 1C,3H 3C,7H 3C,7H     WILLMS SOYBEANS 3C,5H 2C,2H 1C,2H 3C,5G 1C,1H 4C,9G 4C,9G 2C,3H 4C,7G     10P,9G 3C,9G 4C,9G RICE DRY SEEDED 0 2C 1C 0 0 0 2G 0 0 1C 3C,9G 4G G522     SORGHUM 0 0 0 0 0 0 0 0 0 0 3C,9H 7G CHEAT GRASS 0 0 0 0 0 0    0 5G 4G     USN11 SUGARBEET 5H 2G 7H 3G,5I 4H 8H,5I 7H 3G 6G 5H 2C,8H 3H,7G VELVETLEA     F 6G 6G 0 2C,5G 0 3C,8G 5C,8G 3C,8G 5C,9G 4C,8G 4C,9G 7C,9G GIANT     FOXTAIL 0 7G 3G 5G 2G 9G 0 0 0 8H 9G 3C,9G KLAGES BARLEY 0 0 0 0 0 0 0 0     0 0 1C 6G DOWNY BROME       3G 0 0        CMPD 35 (salt) CMPD 35 (salt) CMPD 35 (salt) CMPD 39 CMPD 42 CMPD 47     CMPD 51 CMPD 52       RATE = KG/HA 0.4 0.4 0.4 0.4 0.4 0.4 2 2 COKER COTTON 3H 0 9P,8G     8G,10P 1C 10P,8G 1C,6H 3H,8G CULT MORNINGLRY 3C,8G 0 2C,2H 2C 2C 1C 5G     5C,9G COCKLEBUR 2C,1H 0 2C,2H 2C 3C 1C 2C,7H 3C,9H PURPLE NUTSEDGE 0 0 0     0 0 0 0 LARGE CRABGRASS 0 0 0 0 0 0 2C,9G 3C,9G BARNYARDGRASS 0 0 5H 0 0     0 2C,7G 5C,9G WILD OATS 0 0 0 0 0 0 2C,2G 2C,4G ERA WHEAT 0 0 0 0 0 0     2C,3G 2C,6G G4646 CORN 2H 0 2G 0 0 2G 2C,6H 2C,6G WILLMS SOYBEANS 3C,9G     2G 9G,5I 2C 1H 2C,2H 3C,7H 4C,9G RICE DRY SEEDED 0 0 0 0 0 0 2C,5G 2C,6G     G522 SORGHUM 0 0 0 0 0 0 0 9H CHEAT GRASS   0 0 0 0 5G 2C,6G USN11     SUGARBEET 7G 2G 4H 4H 3H 0 7G 3H,7G VELVETLEAF 3C,5G 0 3C,8H 4H 5C 0 4G     7C,9G GIANT FOXTAIL 2G 0 0 0 2G 0 2C,7G 1C,9G KLAGES BARLEY 0 0 0 0 0 0     0 6G DOWNY BROME 0 0       PREEMERGENCE CMPD 52 CMPD 52 CMPD 56 CMPD 56 CMPD 57 CMPD 58 CMPD 59     CMPD 61 CMPD 66 CMPD 67 CMPD 99 CMPD 101       RATE = KG/HA 0.1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER     COTTON -- 2G 0 5G 0 7G 8G 0 0 0 0 0 0 CULT MORNINGLRY 0 8H 0 4C,9G 0     4C,9G 8G 0 0 0 0 8H 2C,9H COCKLEBUR 2G 2C,2G 0 2G 0 0 3G 0 0 0 0 0 0     PURPLE NUTSEDGE 0 0 0 5G 0 0 0 0 0 0 0 0 0 LARGE CRABGRASS 2C,7H 4C,9H 0     4C,9G 9G 4C,9G 9G 0 0 2C,9G 7G 2C,9G 2G BARNYARDGRASS 0 9C 5G 7C,9H 0 9C     4C,9H 0 0 0 3G 2G 2G WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 8G     0 0 0 2G 0 0 0 0 0 0 0 G4646 CORN 0 0 0 0 0 2G 3G 0 0 0 0 0 0 WILLMS     SOYBEANS 0 0 0 7G 0 3C,9G 4G 0 0 0 1H 0 0 RICE DRY SEEDED 0 0 0 0 0 0 0     0 0 0 0 0 0 G522 SORGHUM 0 8G 0 7G 0 8G 7G 0 0 0 0 0 0 CHEAT GRASS   0     5G  9G 3G   0 3G 0 0 USN11 SUGARBEET 0 5H 0 6G 2H 7H 9G 0 0 5G 7G 3H 0     VELVETLEAF 0 4C,8H 0 4C,9G 0 5C,9G 5G 0 0 2G 0 0 0 GIANT FOXTAIL 3C,9H     9H 0 9H 4C,9G 9H 3C,9G 0 7G 3G 5G 2C,9H 7G KLAGES BARLEY 0 0 0 0 0 2G 0     0 0 0 0 0 0 DOWNY BROME 2G 3C,8G   0   0 0        CMPD 106 CMPD 107 CMPD 108 CMPD 208 CMPD 594 CMPD 594 CMPD 596 CMPD     598 CMPD 603 CMPD 605 CMPD 611 CMPD 618       RATE = KG/HA 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2 COKER     COTTON 0 3G 0 0 0 3G 3G 0 0 0 0 4G CULT MORNINGLRY 0 5C,9G 3H 0 0 0 0 0     0 0 0 2H COCKLEBUR 0 0 0 0 0 0 2G 2G 0  0 0 PURPLE NUTSEDGE 0 0 10E 0 0     0 10E 0 0 0 0 &E LARGE CRABGRASS 4C,9H 5C,9G 9G 0 9G 2U,9G 9H 3C,9G 0 3G     8G 8H BARNYARDGRASS 0 9H 0 0 4C,8H 2C,8G 3C,7H 2G 0 0 2C,6G 5C,9H WILD     OATS 0 0 0 0 0 3G 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 0 0 0 3G G4646     CORN 0 0 0 0 0 2G 2G 0 0 0 0 3G WILLMS SOYBEANS 2G 0 0 0 0 0 0 0 0 0 0 0     RICE DRY SEEDED 0 0 0 0 0 4G 0  0 0 0 2G G522 SORGHUM 0 2H 0 0 0 3G     2C,9H  0 0 0 0 CHEAT GRASS 0   0 2G 3G 0  0 0 0 2G USN11 SUGARBEET 3H 3H     0 2H 2G 4G 3G  0 0 0 7G VELVETLEAF 0 5G 0 0 4G 5G 2G  0 0 0 5G GIANT     FOXTAIL 3C,9G 3C,9G 8H 0 9G 3C,9G 9H  0 0 3C,8G 9H KLAGES BARLEY 3G 0 0     0 0 0 0 0 0 0 0 0 DOWNY BROME  0 0       CMPD 620 CMPD 624 CMPD 627 CMPD 644 CMPD 644 CMPD 646 CMPD 648 CMPD     651 CMPD 653 CMPD 656 CMPD 658 CMPD 659       RATE = KG/HA 0.4 2 0.4 0.4  0.1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER     COTTON 9G 9G 0 0 8G 0 0 0 0 0 5G 0 0 3G CULT MORNINGLRY 2C,8G 9G 2G 0 9G     0 2C 0 0 0 2C,5G 0 0 1C COCKLEBUR 3C,7G 2H 2G  3C,7G 0 0 0 0 0 2H 0 2G 0     PURPLE NUTSEDGE 5G 0 0 0 10E 10E 10E 0 0 0 0 2G 6G 10E LARGE CRABGRASS     9H 9H 9H 0 9H 3C,7H 5C,9H 9G 3C,8G 0 9C 5C,9H 9H 3C,9G BARNYARDGRASS     2C,5H 7C,9H 8H 0 9C 0 5C,9H 0 0 0 3C,9G 0 5G 2C,5G WILD OATS 0 0 0 0     4C,8G 0 2C,5G 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 9G 0 0 0 0 0 2G 0 0 0     G4646 CORN 0 1H 0 0 2C,8H 0 0 0 2G 0 0 0 4G 0 WILLMS SOYBEANS 7G 8G 0 0     8G 0 0 3H 0 0 0 0 2G 0 RICE DRY SEEDED 3G 2G 2G 0 6G 0 0 0 0 0 0 0 0 0     G522 SORGHUM 9G 9G 0 0 3C,9G 0 4G 0 0 0 7G 0 0 0 CHEAT GRASS 0 2G 0 0 7G       0 2G 0 8G 0 0 0 USN11 SUGARBEET 8H 9H 8H 0 9G 0 6H 5H 7H 0 8H 2H 0 0     VELVETLEAF 6G 9H 8G 0 6C,9G 0 2C 2G 4G 0 5C,9G 0 0 7G GIANT FOXTAIL 9H     9H 9H 0 9H 3C,9H 5C,9H 9H 2C,9G 0 5C,9H 4C,9H 7H 3C,9H KLAGES BARLEY 0 0     0 0 3G 0 0 0 3G 0 0 0 0 0 DOWNY BROME      0 3C,5G        CMPD 661 CMPD 669 CMPD 673 CMPD 675 CMPD 721 CMPD 724 CMPD 724 CMPD     726 CMPD 753 CMPD 754 CMPD 782 CMPD 784       RATE = KG/HA 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER     COTTON 0 8G 0 0 0 0 8G 0 3G 0 0 0 CULT MORNINGLRY 0 5C,9H 0 0 3H 2C,8H     9C 0 9G 0 3C,9H 1H COCKLEBUR 0  0  0 0 0 2G 3H 0 0 0 PURPLE NUTSEDGE 0     3G 0 0 0 0 0 0 9G 0 0 5G LARGE CRABGRASS 5G 9H 9H 0 7G 2C,9H 4C,9H 7G 9G     8G 3C,9G 9H BARNYARDGRASS 0 9C 4H 0 0 5C,9H 5C,9H 3C,6G 8G 2H 2C,9H 0     WILD OATS 0 2C 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 2G 0 0 0 0 0 0 0 0 0     G4646 CORN 0 2C,5H 2G 0 0 0 0 2G 0 0 0 0 WILLMS SOYBEANS 0 8G 0 0 0 0 6G     0 3G 0 3G 0 RICE DRY SEEDED 0 0 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 9G 0     0 0 0 6G 0 5G 0 6G 2G CHEAT GRASS 0 0 3G 0 0 0 8G 0 0  0 0 USN11     SUGARBEET 5G 8G 6H 0 2C,3H 5H 8G 2H 8H 3G 9G 5G VELVETLEAF 0 4C,8G 0 0     2G 9G 4C,9G 0 4G 0 2C,8G 4G GIANT FOXTAIL 3G 9H 2C,8G 0 7G 3C,9H 9H     2C,9H 3C,9G 7G 9H 3G KLAGES BARLEY 0 0 2G 0 0 0 0 0 0 0 0 0 DOWNY BROME             0       CMPD 810 CMPD 811 CMPD 815 CMPD 863 CMPD 879 CMPD 905 CMPD 1276 CMPD     1276 CMPD 1276A CMPD 1277        RATE = KG/HA 0.4 0.4 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER COTTON 0     9G 0 0 5G 0 0 0 0 0 0 CULT MORNINGLRY 0 9C 0 0 0 0 0 0 1C,3G 0 0     COCKLEBUR 2G 0   2G 0  0 0 0 0 PURPLE NUTSEDGE 0 10E 0 0 4G 8G 0 0 8G     10E 0 LARGE CRABGRASS 9H 5C,9H 9G 0 4G 9H 0 4C,9H 7G 0 5C,9G BARNYARDGRAS     S 4C,9H 7C,9H 0 0 3G 4C,8H 0 4C,8H 0 0 3C,8H WILD OATS 2G 0 0 0 2G 0 0 0     0 0 0 ERA WHEAT 2G 0 0 0 0 0 0 0 0 0 0 G4646 CORN 0 2G 0 0 0 2G 0 0 0 0     2G WILLMS SOYBEANS 0 7G 0 0 0 2G 0 0 0 0 0 RICE DRY SEEDED 0 0 0 0 0 0 0     0 2G 0 0 G522 SORGHUM 0 8G 0 0 0 0 0 0 0 0 0 CHEAT GRASS 3G 5G 0 0 2G 2G     0 0 0 0 0 USN11 SUGARBEET 9G 8G 0 0 0 5H 0 2H 7G 6G 7H VELVETLEAF 3G     2C,9G 3G 0 0 4G 0 0 4G 8G 3G GIANT FOXTAIL 9H 9H 2G 0 8G 9H 0 4C,9H     2C,9G 0 3C,9H KLAGES BARLEY 0 2G 0 0 0 0 0 0 0 0 0 DOWNY BROME       CMPD 1278 CMPD 1279 CMPD 1280 CMPD 1377 CMPD 1381 CMPD 1304 CMPD 1     CMPD 4 CMPD 9 CMPD 11       RATE = KG/HA 0.4 0.4 0.4 0.4 2 0.4 2 0.4 2 0.4 0.4 0.1 0.4 2 COKER     COTTON 0 0 2G 0 7G 0 8G 0 7G 0 8G 0 5H 9G CULT MORNINGLRY 0 0 2H 2C     2C,3G 0 7H 0 7G 0 9H 0 1C 9G COCKLEBUR 0 0 0 0 2G 0 3G 0 0 0 0 0 0 2C,8G     PURPLE NUTSEDGE 0 0 0 0 9G 0 0 0 3G 5G 0 0 8G 10E LARGE CRABGRASS 0 7G     9H 4C,8H 5C,9H 5C,9G 3C,9G 4C,9H 4C,9G 4C,9G 9C 3C,7H 4C,9H 9H BARNYARDGR     ASS 0 2G 3G 2G 10C 3H 5C,9H 0 5C,9H 1C 10C 4C,6H 9C 5C,9H WILD OATS 0 0     0 0 0 0 0 0 2G 0 0 0 0 8G ERA WHEAT 0 0 0 0 0 0 0 0 0 2G 0 0 2G 2C,9G     G4646 CORN 0 0 0 0 0 0 3G 0 5G 0 0 0 2C,2H 3C,8H WILLMS SOYBEANS 0 0 0 0     5G 0 9G 0 7G 2G 0 0 3C,7H 9G RICE DRY SEEDED 0 0 0 0 0 0 4G 0 0 3G 0 0 0     0 G522 SORGHUM 0 0 0 0 2C,6G 0 7G 3G 9G 0 9H 0 2C,9G 9H CHEAT GRASS 0 0     0 0 0 -- 0 -- 6G 0 0   3C,8G USN11 SUGARBEET 0 3H 5G 2C,6H 8G,5I 2H 8H 0     8H 4H 8H 3H 6H 9H VELVETLEAF 0 5G 5G 3G 7G 3G 8G 5G 7G 5G 7H 0 5C,9H 9G     GIANT FOXTAIL 2G 8G 9H 3C,9H 4C,9H 4C,9H 9H 3C,9H 9H 3C,9H 3C,9H 4C,9H     4C,9H 9H KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 0 4G DOWNY BROME      0     -- 0 --   0 2C,7G       CMPD 13 CMPD 15 CMPD 16 CMPD 17 CMPD 18 CMPD 23 CMPD 33 CMPD 34 CMPD     34 CMPD 34 CMPD 35       RATE = KG/HA 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2 COKER     COTTON 0 0 5G 0 0 0 8G 0 0 0 6G 8H CULT MORNINGLRY 0 0 0 0 1H 0 7G 6G 8G     2C,8G 8H 9H COCKLEBUR 0 0 0 0 0 0 2G 0 0 0 1H 2H PURPLE NUTSEDGE 0 9G     10E 10E 7G 0 0 0 0 0 0 0 LARGE CRABGRASS 5C,9G 3C,9H 8G 9G 10H 9H 8G     3C,9G 4C,9G 4C,9G 9H 10E BARNYARDGRASS 3C,7G 0 5G 3G 5C,9H 3C,6G 2C,8H     5G 5H 3C,8G 6C,9H 7C,9H WILD OATS 0 0 0 0 0 0 0 0 0 0 0 7G ERA WHEAT 0 0     0 0 7G 0 0 0 0 0 0 8G G4646 CORN 3G 0 2G 0 2G 0 0 0 0 2G 0 2C,3H WILLMS     SOYBEANS 0 0 0 0 0 0 4G 0 0 0 2G 7G RICE DRY SEEDED 0 0 2G 0 0 0 2G 0 0     0 0 1C G522 SORGHUM 2H 0 0 0 9G 0 5G 1H 0 0 7G 9H CHEAT GRASS  0 0 0 8G     4G 0    0 8G USN11 SUGARBEET 7H 0 6G 0 7H 3H 7G 5H 2H 4H 5H 9H VELVETLEAF      9C 6G 5G 2G 7G 3G 2G 7G 5G 5C,8G 8H 9H GIANT FOXTAIL 2C,9G 0 9H 6G 9H     5C,9H 9H 3C,9H 3C,9H 3C,9G 9H 9H KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0     DOWNY BROME 4G       0 0 3G        CMPD 35 CMPD 35 CMPD 35 CMPD 35 CMPD 39 CMPD 42 CMPD 47 CMPD 51 CMPD     52       RATE = KG/HA 2 0.4 0.4 0.4 0.4 0.4 0.4 2 2 COKER COTTON 9G  0 8G 0 0 0     5G 9G CULT MORNINGLRY 3C,9H 8G 0 6G 0 0 0 9H 5C,9Z COCKLEBUR 0 0 0 0 0     0 1C,2G 2C,8G PURPLE NUTSEDGE 3G 0 0 0 0 0 0 0 5G LARGE CRABGRASS 10H     3C,9G 0 3C,9G 6G 2C,9G 9G 10H 9H BARNYARDGRASS 9H 7H 0 3C,9G 2G 0 1H     3C,9H 9H WILD OATS 8G 0 0 2G 0 2G 0 2G 2C,8G ERA WHEAT 5G 0 0 0 0 0 0 0     4C,9G G4646 CORN 3G 0 0 0 0 0 3G 0 3C,6G WILLMS SOYBEANS 2C,9G 0 0 9G 0     0 0 0 9G,5I RICE DRY SEEDED 0 0 0 4G 0 0 0 0 8G G522 SORGHUM 2C,9G 0 0     5G 0 0 0 2C,9G 9G CHEAT GRASS 8G   5G 0 0 0 3G 9G USN11 SUGARBEET 9G 3H     0 5H 2H 5H 4H 9H 9G VELVETLEAF 9G 5C,9G 0 7G 0 0 0 9H 9G GIANT FOXTAIL     9H 9H 0 3C,9G 6G 3C,9G 3C,9H 3C,9H 10H KLAGES BARLEY 0 0 0 0 0 0 0 0 7G     DOWNY BROME  0 0

TEST B Postemergence

Three round pans (25 cm diameter by 12.5 cm deep) were filled withSassafras sandy loam soil. One pan was planted with nutsedge (Cyperusrotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassiaobtusifolia), jimsonweed (Datura stramonium), velvetleaf (Abutilontheophrasti), lambsquarters (Chenopodium album), rice (Oryza sativa),and teaweed (Sida spinosa). the second pot was planted with greenfoxtail (Setaria viridis), cocklebur (Xanthium pensylvanicum),morningglory (Ipomoea hederacea), cotton (Gossypium hirsutum),johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusgalli),corn (Zea mays), soybean (Glycine max), and giant foxtail (Setariafaberi). The third pot was planted with wheat (Triticum aestivum),barley (Hordeum vulgare), wild buckwheat (Polygonum convolvulus L.),cheatgrass (Bromus secalinus L.), sugarbeet (Beta vulgaris), wild oat(Avena fatua L.), common chickweed (Stellaria media), blackgrass(Alopecurus myosuroides), and rape (Brassica napus). The plants weregrown for approximately fourteen days, then sprayed postemergence withthe chemicals dissolved in a nonphytotoxic solvent.

Premergence

Three round pans (25 cm diamater by 12.5 cm deep) were filled withSassafras sandy loam soil. One pan was planted with nutsedge tubers,crabgrass, sicklepad, jimsonweed, velvetleaf, lambsquarters, rice andteaweed. The second pot was planted with green foxtail, cocklebur,morningglory cotton, johnsongrass, barnyardgrass, corn, soybean, andgiant foxtail. The third pot was planted with wheat, barley, wildbuckwheat, cheatgrass, sugarbeet, wild oat, viola, blackgrass, and rape.The thee pans were sprayed preemergence with the chemicals dissolved ina nonphytotoxic solvent.

Treated plants and controls were maintained in the greenhouse forapproximately 24 days, then all rated plants were compared to controlsand visually rates for plant response.

Response ratings were based on a scale of 0 to 100 where 0=effect, and100=complete control. A dash (-) response means no test.

Response ratings are contained in Table B.

                                      TABLE B                                     __________________________________________________________________________                CMPD 51  CMPD 669    CMPD 35           CMPD 52                    RATE = G/HA 0250                                                                             0125                                                                             0062                                                                             2000                                                                             1000                                                                             0500                                                                             0250                                                                             0500                                                                             0250                                                                             2000                                                                             1000                                                                             0250                                                                             0062                                                                             2000                                                                             1000                                                                             0250                                                                             0062              __________________________________________________________________________    POST                                                                          GIANT FOXTAIL                                                                             -- 0  0  -- 50 30 0  100                                                                              90 -- 80 70 30 -- 70 50 30                VELVETLEAF  30 0  0  80 50 30 0  100                                                                              70 100                                                                              90 70 50 90 70 50 30                USH11 SUGARBEET                                                                           -- 30 0  -- 80 70 50 70 50 -- 70 60 50 -- 70 50 30                LARGE CRABGRASS                                                                            0 0  0  80 70 50 30 100                                                                              50 100                                                                              100                                                                              90 30 100                                                                              90 90 50                PRICKLY SIDA                                                                              30 0  0  90 70 50 30 100                                                                              90 100                                                                              90 70 50 90 80 70 50                JIMSONWEED   0 0  0  60 40 20 0  60 20 90 70 50  0 90 70 50 30                RICE DRY SEEDED                                                                            0 0  0   0  0  0 0  30 10 60 30  0  0 60 40  0 0                 COCKLEBUR   30 0  0  60 30  0 0  30 -- 90 70 50 30 90 60 30 0                 COKER COTTON                                                                              20 0  0  70 50 30 0  90 70 50 40 30 20 50 40 30 0                 WILLMS SOYBEANS                                                                           -- 0  0  -- 40  0 0  80 60 -- 80 60 20 -- 30  0 0                 BARNYARDGRASS                                                                             0  0  0  70 50 30 0  100                                                                              80 80 60 30  0 90 60 30 0                 WILD OATS   -- 0  0  --  0  0 0  50  0 -- 30  0  0 -- 30  0 0                 IVY MORNINGLORY                                                                           30 0  0  100                                                                              70 50 30 20  0 70 60 50 30 90 70 50 30                ERA WHEAT   -- 0  0  --  0  0 0  10  0 --  0  0  0 -- 50 30 0                 SICKLEPOD   0  0  0  80 30  0 0  50 30 90 70 50 30 70 40 30 0                 JOHNSONGRASS                                                                              0  0  0  30  0  0 0  100                                                                              100                                                                              90 70 50 30 90 70 50 0                 PURPLE NUTSEDGE                                                                           0  0  0  30  0  0 0  80 -- 30  0  0  0 50 30  0 0                 G4646 CORN  -- 0  0  --  0  0 0   0  0 -- 40  0  0 -- 40  0 0                 WILD BUCKWHEAT                                                                            -- 0  0  -- 70 60 50 --  0 -- 70 50 30 -- 70 50 30                BLACKGRASS  -- 0  0  -- 50 30 0  90 60 -- 50 30  0 -- 70 50 30                ALTEX RAPE  -- 0  0  -- 50 30 0  80 60 -- 80 50 30 -- 50 30 0                 KLAGES BARLEY                                                                             -- 0  0  --  0  0 0   0  0 --  0  0  0 -- 30  0 0                 GREEN FOXTAIL                                                                             30 0  0  80 50 30 0  100                                                                              90 90 80 60 30 90 70 50 30                CHEAT GRASS -- 0  0  --  0  0 0        --  0  0  0 -- 50 30 0                 FIELD VIOLET                                                                              -- 0  0  --  0  0 0        --  0  0  0 -- 50 30 0                 LAMBSQUARTER                                                                              70 60 50 90 80 70 60 100                                                                              80 100                                                                              100                                                                              70 50 90 80 70 50                CHICKWEED SPP.                   80 20                                        DOWNY BROME                      40 20                                        __________________________________________________________________________                CMPD 18                                                                             CMPD 35                                                                             CMPD 33  CMP 35      CMPD 1381                                                                              CMPD 1304               RATE = G/HA 0500                                                                             0250                                                                             0250  0500                                                                             0250                                                                             0125                                                                             0500                                                                             0250                                                                             0125                                                                             0062                                                                             0250                                                                             0125                                                                             0062                                                                             0250                                                                             0125                                                                             0062              __________________________________________________________________________    POST                                                                          GIANT FOXTAIL                                                                             30  0 80    30  0  0  0  0  0 -- 60 30  0  0  0  0                VELVETLEAF  80 50 70    90 70 60 90 70 50 30  0  0  0 100                                                                              70 30                USH11 SUGARBEET                                                                           60 50 60    90 80 70 50 30  0 -- 70 50 30 30  0  0                LARGE CRABGRASS                                                                           30 20 80    70 60 50 70 60 50 30  0  0  0  0  0  0                PRICKLY SIDA                                                                              70 50 80    70 60 50 90 60 30  0  0  0  0 50 30  0                JIMSONWEED  40  0 50    90 70 50 30 20  0  0 60 50 30 60 30  0                RICE DRY SEEDED                                                                           40 30  0     0  0  0  0  0  0  0  0  0  0  0  0  0                COCKLEBUR   40 20 30    30 20  0 30  0  0  0 50 30  0 50 30  0                COKER COTTON                                                                              60 40 90    30 30 30 60 40 30  0 50 30  0 50 30  0                WILLMS SOYBEANS                                                                           30 30 30    60 50 40 60 40 30 -- 30  0  0 30  0  0                BARNYARDGRASS                                                                             10 10 90     0  0  0  0  0  0  0  0  0  0  0  0  0                WILD OATS   30  0  0    30  0  0  0  0  0 --  0  0  0  0  0  0                IVY MORNINGLORY                                                                           30 20 70    80 70 50 50 30  0  0 50 30  0 30  0  0                ERA WHEAT    0  0  0     0  0  0  0  0  0 --  0  0  0  0  0  0                SICKLEPOD   40 20 20    50 30 20 50 30  0  0 30  0  0 50 30  0                JOHNSONGRASS                                                                              40  0 90     0  0  0 50 30  0  0 30  0  0  0  0  0                PURPLE NUTSEDGE                                                                           30  0  0     0  0  0 60 30  0  0 30  0  0 70 50 30                G4646 CORN   0  0  0     0  0  0  0  0  0 --  0  0  0  0  0  0                WILD BUCKWHEAT                                                                            40 -- 50    60 30  0 80 50 30 -- 50 30  0 60 30  0                BLACKGRASS  40  0 40    30  0  0 50 30  0 -- 70 50 30 30  0  0                ALTEX RAPE  100                                                                              80 50    70 50 30 30  0  0 -- 30  0  0  0  0  0                KLAGES BARLEY                                                                             10  0  0     0  0  0  0  0  0 --  0  0  0  0  0  0                GREEN FOXTAIL                                                                             40  0 80    30  0  0 50 30  0  0 30  0  0  0  0  0                CHEAT GRASS 30 10        0  0  0  0  0  0 --  0  0  0                         FIELD VIOLET            90 60 30                                              LAMBSQUARTER                                                                              100                                                                              50 60    80 70 50 50 30  0  0  0  0  0 80 50  0                CHICKWEED SPP.                                                                            50  0  0             60 30  0 --  0  0  0 60 30  0                DOWNY BROME        0                                   0  0  0                __________________________________________________________________________                               CMPD 810    CMPD 9   CMPD 107 CMPD 13                             RATE = G/HA 0500                                                                             0250                                                                             0125                                                                             0062                                                                             0500                                                                             0250                                                                             0125                                                                             0500                                                                             0250                                                                             0125                                                                             0250                                                                             0125              __________________________________________________________________________                   POST                                                                          GIANT FOXTAIL                                                                             80 20  0  0 80 50 30 60 20  0 20  0                               VELVETLEAF  60 30 20  0 70 40 -- 80 80 70 70 60                               USH11 SUGARBEET                                                                           20 20  0 -- 90 50 40 90 90 80 80 40                               LARGE CRABGRASS                                                                           40 20  0  0 30 20  0 30 30 --  0  0                               PRICKLY SIDA                                                                              30 20  0  0 70 60 30 100                                                                              90 80 60 40                               JIMSONWEED  30 20  0  0 50 30 30 90 50 30 40 30                               RICE DRY SEEDED                                                                           30  0  0  0 30  0  0 10  0  0  0  0                               COCKLEBUR   30 20  0  0 40 40 30 50 40 20 30  0                               COKER COTTON                                                                              30 20 10 10 80 60 30 90 70 60 90 80                               WILLMS SOYBEANS                                                                           80 30  0  0 30 20  0 -- 60  0 40  0                               BARNYARDGRASS                                                                             30 20  0  0 100                                                                              90 30 100                                                                              80 70 20  0                               WILD OATS   30 20  0 -- 30 20 10 20 20 -- 30  0                               IVY MORNINGLORY                                                                            0  0  0  0 50 --  0 100                                                                              90 60 70 40                               ERA WHEAT   20  0  0  0  0  0  0  0  0  0 10  0                               SICKLEPOD   20  0  0  0 70 60 60 90 40 20 40 20                               JOHNSONGRASS                                                                              20  0  0  0 50 30  0  0  0  0  0   0                              PURPLE NUTSEDGE                                                                            0  0  0  0 --  0  0 70 70  0  0  0                               G4646 CORN  30 20  0  0  0  0  0  0  0  0  0  0                               WILD BUCKWHEAT                                                                            60 20  0 -- 60 40 30 90 70 70 50 30                               BLACKGRASS  80 30 20 -- 70 10  0 70 40  0 80 30                               ALTEX RAPE  80 30 20 -- 60 40  0 70 60 60 30  0                               KLAGES BARLEY                                                                             30 20  0 --  0  0  0  0  0  0  0  0                               GREEN FOXTAIL                                                                             30 20  0  0 100                                                                              70 30 80 40 30 40  0                               CHEAT GRASS  0  0  0 --                                                       LAMBSQUARTER                                                                              80 70 30  0 -- 90 50 80 80 60 50 --                               CHICKWEED SPP.                                                                            80 20  0 -- 70 70 30 80 50 40 50  0                               DOWNY BROME              0  0  0  0  0  0  0  0                __________________________________________________________________________                  CMPD 51         CMPD 669      CMPD 35                           RATE = G/HA  1000                                                                             0500                                                                              0250                                                                             0125                                                                              0062                                                                             2000                                                                              1000                                                                             0500                                                                              0250                                                                             0500                                                                              0125                                                                             2000                                                                             1000                                                                             0250                                                                             0062              __________________________________________________________________________    PRE                                                                           GIANT FOXTAIL                                                                              100                                                                              100 90 60  30 100 100                                                                              100 100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              90                VELVETLEAF   80 50  30  0   0 50  30  0   0 100 90 90 80 70 60                USH11 SUGARBEET                                                                            80 70  60 50  30 70  50 30   0 90  20 60 40 30  0                LARGE CRABGRASS                                                                            100                                                                              90  70 50  30 100 100                                                                              90  80 100 100                                                                              100                                                                              100                                                                              100                                                                              100               PRICKLY SIDA 90 80  70 50  30 90  70 50  30 100 100                                                                              90 80 70 60                JIMSONWEED   80 60  40 30   0 70  50 40  30 70  50 100                                                                              90 80 60                RICE DRY SEEDED                                                                             0  0   0  0   0  0   0  0    0                                                                              10   0  0  0  0  0                COCKLEBUR    50 30   0  0   0 40  20  0   0 20   0 50 40 30  0                COKER COTTON  0  0   0  0   0  0   0  0   0 100 20 80 70 60 30                WILLMS SOYBEANS                                                                             0  0   0  0   0  0   0  0   0 10   0 90 80 30  0                BARNYARDGRASS                                                                              100                                                                              80  50 30   0 100 100                                                                              50  30 100 60 100                                                                              100                                                                              100                                                                              60                WILD OATS     0  0   0  0   0  0   0  0   0 40  20  0  0  0  0                IVY MORNINGLORY                                                                             0  0   0  0   0 40   0  0   0  0   0 80 60 40  0                ERA WHEAT     0  0   0  0   0  0   0  0   0 20   0  0  0                                                                                   0                SICKLEPOD    60 30   0  0   0 30   0  0   0 50   0 90 70 30  0                JOHNSONGRASS 90 70  50 30   0 90  80 50  30 100 50 100                                                                              100                                                                              90 70                PURPLE NUTSEDGE                                                                             0  0   0  0   0  0   0  0   0 50   0  0  0  0  0                G4646 CORN    0  0   0  0   0  0   0  0   0 40  10 60 40 20  0                WILD BUCKWHEAT                                                                             60 30   0  0   0 70  50 30   0 100 30 80 70 50 30                BLACKGRASS   60 30   0  0   0 70  50 30   0 100 80 90 80 60 30                ALTEX RAPE   70 60  50 30   0 70  50 30   0 80  40 90 70 50 30                KLAGES BARLEY                                                                               0  0   0  0   0  0   0  0   0  0   0  0  0  0  0                GREEN FOXTAIL                                                                              100                                                                              100 90 70  50 100 100                                                                              100 100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100               CHEAT GRASS   0  0   0  0   0 30   0  0   0        60 30  0  0                FIELD VIOLET 90 70  50 30   0 80  30  0   0        80 70 50 30                LAMBSQUARTER 100                                                                              100 90 80  70 100 90 70  50 100 90 100                                                                              100                                                                              90 80                CHICKWEED SPP.                              40  --                            DOWNY BROME                                 80  40                            __________________________________________________________________________                 CMPD 52       CMPD 18       CMPD 35    CMPD 33                   RATE = G/HA  2000                                                                             1000                                                                              0250                                                                              0062                                                                             0500                                                                              0250                                                                             0125                                                                              0062                                                                             0250                                                                              0125                                                                             0062                                                                              0500                                                                             0250                                                                              0125               __________________________________________________________________________    PRE                                                                           GIANT FOXTAIL                                                                              100                                                                              100 90  60 100 100                                                                              90  30 100 100                                                                              100 100                                                                              90  80                 VELVETLEAF   90 70  50  30 70  20 --  -- --  90 30  90 80  70                 USH11 SUGARBEET                                                                            80 50  30   0 50  30 20  -- 50  20  0  80 50  30                 LARGE CRABGRASS                                                                            100                                                                              100 100 80 100 100                                                                              100 50 100 100                                                                              60  90 70  50                 PRICKLY SIDA 90 80  80  70 90  90 80  50 --  70 60  60 30   0                 JIMSONWEED   100                                                                              100 70  50 70  20  0   0  0   0  0  70 50  30                 RICE DRY SEEDED                                                                            50 30   0   0 10   0  0  30 30  10  0   0  0   0                 COCKLEBUR    100                                                                              100 50  30 20   0  0  30  0  --  0  30  0   0                 COKER COTTON 80 60  20   0 10   0  0  -- 50  20  0  30  0   0                 WILLMS SOYBEANS                                                                            80 60   0   0 10   0  0   0 40  10  0   0  0   0                 BARNYARDGRASS                                                                              100                                                                              100 80  30 100 60 20   0 80  30 10  100                                                                              90  80                 WILD OATS    30 20   0   0 30   0 --  -- 10   0  0   0  0   0                 IVY MORNINGLORY                                                                            80 60  40   0 40  30 30   0 50  40 40  60 40  20                 ERA WHEAT    50 30   0   0 10   0  0   0  0  --  0   0  0   0                 SICKLEPOD    90 60  30   0 100 50 30   0 90  40 30  50 30   0                 JOHNSONGRASS 100                                                                              90  80  50 90  60 30   0 70  10  0  50 30   0                 PURPLE NUTSEDGE                                                                            70 30   0   0                0   0  0   0  0   0                 G4646 CORN   60 30   0   0 10  10 10   0  0   0  0   0  0   0                 WILD BUCKWHEAT                                                                             80 50  30   0 50  30 30   0 40   0 --   0  0   0                 BLACKGRASS   90 70  50  30 90  80 80  30 50  -- 10  30  0   0                 ALTEX RAPE   70 40  20   0 30  20 20  -- 40  40 30  90 80  70                 KLAGES BARLEY                                                                              30 20   0   0 30  30 20  10 10   0  0   0  0   0                 GREEN FOXTAIL                                                                              100                                                                              100 90  70 100 100                                                                              100 30 100 100                                                                              70  100                                                                              90  80                 CHEAT GRASS  70 50  30   0 40  20 20  20             0  0   0                 FIELD VIOLET 100                                                                              90  30   0                          70 50  30                 LAMBSQUARTER 100                                                                              100 90  80 100 90 80  60 100 70 60  100                                                                              100 100                CHICKWEED SPP.             50  20 --  -- 40  30  0                            DOWNY BROME                              30  10  0                            __________________________________________________________________________                 CMPD 35       CMPD 1381 CMPD 1304  CMPD 810                      RATE = G/HA  0500                                                                             0250                                                                              0125                                                                              0062                                                                             0250                                                                              0125                                                                             0062                                                                             0250                                                                              0125                                                                             0062                                                                              0500                                                                              0250                                                                             0125                                                                              0062               __________________________________________________________________________    PRE                                                                           GIANT FOXTAIL                                                                              100                                                                              100 100 90 100 100                                                                              90 100 100                                                                              70                                VELVETLEAF   90 80  60  50  0   0  0 30   0  0  50  40 20   0                 USH11 SUGARBEET                                                                            70 50  40   0 90  70 50 50  30  0  40  30 30  20                 LARGE CRABGRASS                                                                            100                                                                              100 100 100                                                                              100 100                                                                              100                                                                              100 90 80  100 90 90  20                 PRICKLY SIDA 70 60  60  50 30   0  0 70  50 30  60  50 30  20                 JIMSONWEED   40 40  20   0 50  30  0 30   0  0  50  40 30  30                 RICE DRY SEEDED                                                                            10 10   0   0  0   0  0  0   0  0   0   0  0   0                 COCKLEBUR    30 30   0   0 50  30  0 50  30  0  30  20  0   0                 COKER COTTON 60 10   0   0 30  30 30  0   0  0   0   0  0   0                 WILLMS SOYBEANS                                                                            10 10   0   0  0   0  0  0   0  0  20   0  0   0                 BARNYARDGRASS                                                                              100                                                                              90  40  30 80  50 30 70  30  0  100 90 70  40                 WILD OATS    40 30  20   0 50  30  0 50  30  0  20   0  0   0                 IVY MORNINGLORY                                                                            20  0   0   0 60  30  0  0   0  0  30  20  0   0                 ERA WHEAT    20 20  10   0 30   0  0 30   0  0  20   0  0   0                 SICKLEPOD    30 20   0   0  0   0  0  0   0  0   0   0  0   0                 JOHNSONGRASS 90 80  40  40 70  30  0 40   0  0  50  40 30  20                 PURPLE NUTSEDGE                                                                            100                                                                              20   0   0 30   0  0  0   0  0   0   0  0   0                 G4646 CORN    0  0   0   0  0   0  0  0   0  0  30  20  0   0                 WILD BUCKWHEAT                                                                             50 30   0   0  0   0  0 70  50 30  30   0  0   0                 BLACKGRASS   60 40  40  30 50  40 30 50  30  0  70  30 20   0                 ALTEX RAPE   80 80  70  30 70  50 30  0   0  0  30  20  0   0                 KLAGES BARLEY                                                                              20  0   0   0  0   0  0  0   0  0  30   0  0   0                 GREEN FOXTAIL                                                                              100                                                                              100 100 60 100 100                                                                              80 100 100                                                                              70  100 100                                                                              100 90                 CHEAT GRASS  40 30   0   0 30   0  0            40  30 20   0                 LAMBSQUARTER 100                                                                              90  80  80 70  50 30 50  30  0  90  80 50  40                 CHICKWEED SPP.                                                                             30  0   0   0 70  50 30  0   0  0  30   0  0   0                 DOWNY BROME                           0   0  0                                __________________________________________________________________________                               CMPD 9        CMPD 107    CMPD 13                                 RATE = G/HA 0500                                                                              0250                                                                             0125                                                                              0062                                                                             0500                                                                             0250                                                                             0125                                                                             0062                                                                             0250                                                                              0125                                                                             0062              __________________________________________________________________________                   PRE                                                                           GIANT FOXTAIL                                                                             100 100                                                                              100 40 100                                                                              100                                                                              90 70 100 90 40                               VELVETLEAF  100 70 40  20 80 40 30 20 40  20  0                               USH11 SUGARBEET                                                                           90  70 60  40 90 80 60 10 90  80 50                               LARGE CRABGRASS                                                                           100 100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100 100                                                                              100                              PRICKLY SIDA                                                                              90  50 10   0 80 80 70  0 90  60 40                               JIMSONWEED  80  50 30  30 50 40 20  0 50  30  0                               RICE DRY SEEDED                                                                            0   0  0   0  0  0  0  0  0   0  0                               COCKLEBUR   30   0  0   0 10  0  0  0 20   0  0                               COKER COTTON                                                                              30  10 --   0 10  0  0  0  0   0  0                               WILLMS SOYBEANS                                                                           10   0  0   0  0  0  0  0  0   0  0                               BARNYARDGRASS                                                                             100 100                                                                              30   0 100                                                                              90 40  0 90  40  0                               WILD OATS    0   0  0   0 30  0  0  0  0   0  0                               IVY MORNINGLORY                                                                           20   0  0   0 50 30  0  0  0   0  0                               ERA WHEAT    0   0  0   0  0  0  0  0 20   0  0                               SICKLEPOD   50  20  0   0 80 40 --  0 30   0  0                               JOHNSONGRASS                                                                              100 90 50  40 100                                                                              90 40 20 60  50 30                               PURPLE NUTSEDGE                                                                            0   0  0   0 30 --  0  0  0   0  0                               G4646 CORN  10   0  0   0 10  0  0  0  0   0  0                               WILD BUCKWHEAT                                                                            80  50 30   0 70 60 50 20 80  40 30                               BLACKGRASS  90  50 20   0 70 50 30 10 40  30 10                               ALTEX RAPE  90  70 50  30 70 60 60 40 70  60 50                               KLAGES BARLEY                                                                              0   0  0   0  0  0  0  0  0   0  0                               GREEN FOXTAIL                                                                             100 100                                                                              100 40 100                                                                              100                                                                              100                                                                              90 100 50 20                               LAMBSQUARTER                                                                              100 100                                                                              90  80 100                                                                              90 90 80 100 90 80                               CHICKWEED SPP.                                                                            40  10  0   0 70 40  0  0 30   0  0                               DOWNY BROME 40  20  0   0  0  0  0  0 20   0  0                __________________________________________________________________________

TEST C

Sixteen cm diameter Airlite plastic pots were partially filled with Tamasilt loam soil and the soil saturated with water. Japonica and Indicarice seedlings a the 2.0 to 2.5 leaf stage were transplanted into 1/3 ofthe pots. Into another third of the pots were transplanted seedling orsprouted tubers of water plantain (Alisma trivale), Scripus (Scripuspaludosus), Cyperus (Cyperus esculentus), and arrowhead (Sagittariaspp.). The remaining pots were planted with barnyardgrass (Echinochloacrusgalli) seeds and sprouted tubes of water chestnut (Eleocharis spp.).These weeds all represent major rice weeds or genera of weeds importantin rice. Three to four days after planting, the water level was raisedto 3 cm (about 1200 ml/pot) and maintained a this level throughout thetest. Chemical treatments were applied directly to the paddy water,within 24 hours of raising the water, after being formulated in anonphytotoxic solvent. The pots were maintained in the greenhouse. Ratesof application and plant response ratings made 21 days after treatmentare summarized in Table C.

                  TABLE C                                                         ______________________________________                                        CMPD 669                                                                      RATE = G/HA    1000    0500   0250  0125 0064                                 ______________________________________                                        BARNYARDGRASS  100     90     98    98   90                                   WATERCHESTNUT  0       0      0     0    0                                    ARROWHEAD      0       0      0     0    0                                    SCIRPUS        30      0      0     0    0                                    YELLOW NUTSEDGE                                                                              80      60     0     0    0                                    WATER PLAINTAIN                                                                              0       0      0     0    0                                    RICE JAP EFF   0       0      0     0    0                                    RICE INDICA EFF                                                                              0       0      0     0    0                                    ______________________________________                                        CMPD 35                                                                       RATE = G/HA    1000    0500   0250  0125 0064                                 ______________________________________                                        BARNYARDGRASS  95      100    80    100  70                                   WATERCHESTNUT  0       0      60    40   60                                   ARROWHEAD      95      50     40    0    0                                    SCIRPUS        50      0      0     0    0                                    YELLOW NUTSEDGE                                                                              100     95     60    0    0                                    WATER PLAINTAIN                                                                              60      40     40    0    0                                    RICE JAP EFF   20      0      0     0    0                                    RICE INDICA EFF                                                                              20      0      0     0    0                                    ______________________________________                                        CMPD 35                                                                       RATE = G/HA    2000    0500   0125  0032                                      ______________________________________                                        RICE JAP TOL   50      50     20    0                                         RICE INDICA TOL                                                                              60      55     55    0                                         ______________________________________                                        CMPD 18                                                                       RATE =  G/HA   1000    0500   0250  0125 0064                                 ______________________________________                                        BARNYARDGRASS  60      40     0     0    0                                    WATERCHESTNUT  50      40     0     0    0                                    ARROWHEAD      35      20     0     0    0                                    SCIRPUS        0       0      0     0    0                                    WATER PLAINTAIN                                                                              40      20     0     0    0                                    RICE JAP EFF   70      50     0     0    0                                    RICE INDICA EFF                                                                              50      30     0     0    0                                    ______________________________________                                        CMPD 50                                                                       RATE = G/HA    1000    0500   0250  0125 0064                                 ______________________________________                                        BARNYARDGRASS  70      70     60    0    0                                    WATERCHESTNUT  0       0      0     0    0                                    ARROWHEAD      50      30     0     0    0                                    SCIRPUS        0       0      0     0    0                                    YELLOW NUTSEDGE                                                                              50      30     0     0    0                                    WATER PLAINTAIN                                                                              0       0      0     0    0                                    RICE JAP EFF   70      60     30    0    0                                    RICE INDICA EFF                                                                              80      70     30    40   0                                    ______________________________________                                        CMPD 33                                                                       RATE = G/HA    1000    0500   0250  0125 0064                                 ______________________________________                                        BARNYARDGRASS  95      70     80    10   0                                    WATERCHESTNUT  0       0      0     0    0                                    ARROWHEAD      0       0      0     0    0                                    SCIRPUS        0       0      0     0    0                                    YELLOW NUTSEDGE                                                                              40      0      0     0    0                                    WATER PLAINTAIN                                                                              0       0      0     0    0                                    RICE JAP EFF   60      30     0     0    0                                    RICE INDICA EFF                                                                              70      30     0     0    0                                    ______________________________________                                        CMPD 1381                                                                     RATE = G/HA    1000    0500   0250  0125 0064                                 ______________________________________                                        BARNYARDGRASS  100     100    60    55   55                                   WATERCHESTNUT  0       0      0     0    0                                    ARROWHEAD      0       0      0     0    0                                    SCIRPUS        30      0      0     0    0                                    YELLOW NUTSEDGE                                                                              50      40     0     0    0                                    WATER PLAINTAIN                                                                              0       0      0     0    0                                    RICE JAP EFF   60      40     20    0    0                                    RICE INDICA EFF                                                                              60      40     20    0    0                                    ______________________________________                                        CMPD 1304                                                                     RATE = G/HA    1000    0500   0250  0125 0064                                 ______________________________________                                        BARNYARDGRASS  100     98     100   100  85                                   WATERCHESTNUT  50      0      0     0    0                                    ARROWHEAD      30      0      0     0    0                                    SCIRPUS        80      70     65    0    0                                    YELLOW NUTSEDGE                                                                              0       0      0     0    0                                    WATER PLAINTAIN                                                                              65      0      0     0    0                                    RICE JAP EFF   40      0      0     0    0                                    RICE INDICA EFF                                                                              40      0      0     0    0                                    ______________________________________                                        CMPD 107                                                                      RATE = G/HA    1000    0500   0250  0125 0064                                 ______________________________________                                        BARNYARDGRASS  80      90     40    0    0                                    WATERCHESTNUT  30      60     40    0    0                                    ARROWHEAD      70      95     0     0    0                                    SCIRPUS        80      80     60    0    0                                    YELLOW NUTSEDGE                                                                              95      30     50    0    0                                    WATER PLAINTAIN                                                                              80      60     0     0    0                                    RICE JAP EFF   50      40     30    0    0                                    RICE INDICA EFF                                                                              50      40     30    0    0                                    ______________________________________                                    

TEST D

The Corn and Sorghum Herbicide Test included the following species inboth the preemergence and postemergence evaluations:

    ______________________________________                                                  SPECIES                                                             Category    Common Name  Scientific Name                                      ______________________________________                                        Crops       Corn         Zea mays                                                         Soybean      Glycine max                                                      Sorghum      Sorghum bicolor                                      Grasses     Green foxtail                                                                              Setaria viridis                                                  Giant foxtail                                                                              Setaria faberii                                                  Johnsongrass Sorghum halepense                                                Barnyardgrass                                                                              Echinochloa crus-galli                                           Fall panicum Panicum dichotomiflorum                                          Crabgrass    Digitaria sanguinalis                                            Nutsedge     Cyperus rotundus                                     Broadleaves Cocklebur    Xanthium pensylvanicum                                           Morningglory Ipomoea hederacea                                                Velvetleaf   Abutilon theophrasti                                             Jimsonweed   Datura stramonium                                                Lambsquarters                                                                              Chenopodium album                                                Pigweed      Amaranthus retroflexus                                           Smartweed    Polygonum persicaris                                 ______________________________________                                    

Postemergence

Postemergence platings were grown in Sassafras sandy loam soil. Corn andsoybeans were grown in separate 25 cm diameter containers. Sorghum andthe seven grass weed species were grown in two 18 cm diametercontainers, 4 species per container. The seven broadleaf weed specieswere also grown in two 18 cm diameter containers, 4 species in onecontainer, 3 species in the second container. One additional planting ofcorn in an 18 cm diameter container was made. One additional planting ofcorn in an 18 cm diameter container was made. The soil surface of thisadditional container of corn was covered with the absorbent, perlite,before spray treatment so that test chemicals would enter the plant onlyvia the foliage.

The plants were grown 10-21 days, dependent upon the species and thensprayed postmergence with the test chemicals dissolved in a nonpytotoxicsolvent.

Postemergence

Preemergence plantings were grown in fertilized Tama slit loam soil.These plantings are identical to those described in the postemergencesection, with the exception of the corn planting having perlite coveringthe soil surface. These plantings were made the day of or the day beforespraying the test chemicals dissolved in a nonphytotoxic solvent.

Evaluation

Treated plants and controls were maintained in the greenhouse for 2 to 4weeks. Visual planting response ratings were made on a percentage scaleof 0 to 100 in comparison with a control where 0 =no injury, and 100=death.

The results are shown in Table D.

                  TABLE D                                                         ______________________________________                                        CMPD 50                                                                                     RATE GM/HA                                                                    0500  0250     0125    0064                                     ______________________________________                                        PREEMERGENCE                                                                  G4646 CORN      0       0        0     0                                      WILLMS SOYBEANS 20      0        0     0                                      GREEN FOXTAIL   85      50       30    0                                      GIANT FOXTAIL   85      75       65    20                                     FALL PANICUM    95      60       35    20                                     LARGE CRABGRASS 100     100      75    40                                     BARNYARDGRASS   45      20       0     0                                      JOHNSONGRASS    95      90       70    35                                     G522 SORGHUM    0       0        0     0                                      PURPLE NUTSEDGE 30      0        0     0                                      VELVETLEAF      65      40       25    0                                      COCKLEBUR       25      0        0     0                                      LADY SMARTWEED  40      20       0     0                                      LAMBSQUARTER    90      75       35    0                                      REDROOT PIGWEED 100     85       40    0                                      IVY MORNINGLORY 65      40       30    0                                      JIMSONWEED      70      50       25    0                                      POSTEMERGENCE                                                                 G4646 CORN      20      0                                                     WILLMS SOYBEANS 65      35                                                    GREEN FOXTAIL   0       0                                                     GIANT FOXTAIL   0       0                                                     FALL PANICUM    35      20                                                    LARGE CRABGRASS 100     70                                                    BARNYARDGRASS   0       0                                                     JOHNSONGRASS    40      20                                                    G522 SORGHUM    0       0                                                     PURPLE NUTSEDGE 0       0                                                     VELVETLEAF      25      0                                                     COCKLEBUR       40      25                                                    LADY SMARTWEED  40      30                                                    LAMBSQUARTER    80      65                                                    REDROOT PIGWEED 95      65                                                    IVY MORNINGLORY 60      20                                                    JIMSONWEED      45      20                                                    PERLITE CORN    0       0                                                     ______________________________________                                        CMPD 33                                                                                      RATE GM/HA                                                                   1000  0500     0250                                             ______________________________________                                        PREEMERGENCE                                                                  G4646 CORN      0       0        0                                            WILLMS SOYBEANS 0       0        0                                            GREEN FOXTAIL   0       0        0                                            GIANT FOXTAIL   0       0        0                                            FALL PANICUM    0       0        0                                            LARGE CRABGRASS 0       0        0                                            BARNYARDGRASS   0       0        0                                            JOHNSONGRASS    0       0        0                                            G522 SORGHUM    0       0        0                                            PURPLE NUTSEDGE 0       0        0                                            VELVETLEAF      0       0        0                                            COCKLEBUR       0       0        0                                            LADY SMARTWEED  0       0        0                                            LAMBSQUARTER    0       0        0                                            REDROOT PIGWEED 0       0        0                                            IVY MORNINGLORY 0       0        0                                            JIMSONWEED      0       0        0                                            POSTEMERGENCE                                                                 G4646 CORN      0       0        0                                            WILLMS SOYBEANS 0       0        0                                            GREEN FOXTAIL   0       0        0                                            GIANT FOXTAIL   0       0        0                                            FALL PANICUM    0       0        0                                            LARGE CRABGRASS 0       0        0                                            BARNYARDGRASS   0       0        0                                            JOHNSONGRASS    0       0        0                                            G522 SORGHUM    0       0        0                                            PURPLE NUTSEDGE 0       0        0                                            VELVETLEAF      0       0        0                                            COCKLEBUR       0       0        0                                            LADY SMARTWEED  0       0        0                                            LAMBSQUARTER    0       0        0                                            REDROOT PIGWEED 0       0        0                                            IVY MORNINGLORY 0       0        0                                            JIMSONWEED      0       0        0                                            PERLITE CORN    0       0        0                                            ______________________________________                                        CMPD 35                                                                                     RATE GM/HA                                                                    0500   0250    0125    0064                                     ______________________________________                                        PREEMERGENCE                                                                  G4646 CORN      0       0        0     0                                      WILLMS SOYBEANS 0       0        0     0                                      GREEN FOXTAIL   100     80       70    30                                     GIANT FOXTAIL   100     80       50    0                                      FALL PANICUM    100     80       50    0                                      LARGE CRABGRASS 100     95       70    50                                     BARNYARDGRASS   100     40       60    0                                      JOHNSONGRASS    100     100      30    30                                     G522 SORGHUM    0       0        0     0                                      PURPLE NUTSEDGE 50      0        0     --                                     VELVETLEAF      100     100      70    60                                     COCKLEBUR       20      0        0     0                                      LADY SMARTWEED  100     50       30    0                                      LAMBSQUARTER    80      60       30    30                                     REDROOT PIGWEED 98      50       0     0                                      IVY MORNINGLORY 30      0        0     0                                      JIMSONWEED      30      80       0     0                                      POSTEMERGENCE                                                                 G4646 CORN      0       0                                                     WILLMS SOYBEANS 30      10                                                    GREEN FOXTAIL   40      0                                                     GIANT FOXTAIL   60      0                                                     LARGE CRABGRASS 30      30                                                    BARNYARDGRASS   60      40                                                    JOHNSONGRASS    50      0                                                     G522 SORGHUM    50      0                                                     PURPLE NUTSEDGE 0       0                                                     VELVETLEAF      90      60                                                    COCKLEBUR       30      0                                                     LADY SMARTWEED  50      50                                                    LAMBSQUARTER    20      0                                                     REDROOT PIGWEED 70      30                                                    IVY MORNINGLORY 30      20                                                    JIMSONWEED      20      20                                                    PERLITE CORN    0       0                                                     ______________________________________                                    

TEST E

Seeds of the following crops and weeds are sown into 15 cm potscontaining Sassafras sandy loam soil: wheat (Triticum sestivum cv.Park), barley (Hordeum vulgare cv. Bonansa), sugarbeet (Beta vulgariscv. USH-11), rapeseed (Brassica napus cv. Jet Neuf), black nightshade(Solanum nigrum), chickweed (Stellaria media), lambsquarter (Chenopodiumalbum), Galium aparine, knotweed (Polygonium aviculare), Kochiascoparia, Matricaria indora, redroot pigweed (Amaranthus retroflexus),smartweed (Polygonum persicaria), speedwell (Veronica persica), wildbuckwheat (Polygonum convolvulus), wild mustard (Brassica spp.), wildradish (Raphanus raphanistrum), annual bluegrass (Po annua), annualryegrass (Lolium multiflorum), blackgrass (Alopercurus mysuroides),green foxtail (Setaria viridis), and wild oats (Avena fatua). Compoundsare formulated in a nonphytotoxic solvent and applied to the plants as afoliar spray or applied to the soil surface. Plants are treated at twostages: preemergence, or postemergence when the sugarbeets are at the2-3 true leaf stage. Plants are grown in a temperature-controlledgreenhouse for the duration of the test.

Weed control and crop injury are evaluated visually at 3-4 aftercompound application, using a scale of 0 to 100%, where 0=no injury and100 =complete death of the plant. All plants are rated with respect tountreated plants (checks) grown in the greenhouse under identicalconditions to the treated plants.

The results are shown in Table E.

                  TABLE E                                                         ______________________________________                                        CMPD 51                                                                                     RATE GM/HA                                                                    0500  0250     0125    0064                                     ______________________________________                                        POSTEMERGENCE                                                                 PARK WHEAT      0       0        0     0                                      BONANZA BARLEY  0       0        0     0                                      BLACK NIGHTSHAD 60      40       0     0                                      CMN CHICKWEED   0       0        0     0                                      LAMBSQUARTER    40      20       0     0                                      CTCHWD BEDSTRAW 50      0        0     0                                      KOCHIA          0       0        0     0                                      SNTLS CHAMOMILE 60      40       20    0                                      REDROOT PIGWEED 90      60       50    30                                     PERSN SPEEDWELL 40      20       0     0                                      WILD BUCKWHEAT  0       0        0     0                                      MUSTARD SPP.    30      30       30    0                                      WILD RADISH     60      30       30    0                                      ANN. BLUEGRASS  50      20       0     0                                      ITALN. RYEGRASS 0       20       20    0                                      BLACKGRASS      0       0        0     0                                      GREEN FOXTAIL   0       0        0     0                                      WILD OATS       0       0        0     0                                      JET RAPE        20      0        0     0                                      PREEMERGENCE                                                                  PARK WHEAT      0                                                             BONANZA BARLEY  30                                                            BLACK NIGHTSHAD 100                                                           CMN CHICKWEED   0                                                             LAMBSQUARTER    100                                                           CTCHWD BEDSTRAW 0                                                             KOCHIA          70                                                            SNTLS CHAMOMILE 100                                                           REDROOT PIGWEED 70                                                            PERSN SPEEDWELL 20                                                            WILD BUCKWHEAT  0                                                             MUSTARD SPP.    0                                                             WILD RADISH     0                                                             ANN. BLUEGRASS  20                                                            ITALN. RYEGRASS 0                                                             BLACKGRASS      0                                                             GREEN FOXTAIL   100                                                           WILD OATS       20                                                            JET RAPE        0                                                             ______________________________________                                         CMPD 644                                                                                   RATE GM/HA                                                                    0500  0250     0125    0064                                     ______________________________________                                        POSTEMERGENCE                                                                 PARK WHEAT      40      30       20    0                                      BONANZA BARLEY  40      20       20    0                                      BLACK NIGHTSHAD 20      10       0     0                                      CMN CHICKWEED   0       0        0     0                                      LAMBSQUARTER    40      20       0     0                                      CTCHWD BEDSTRAW 30      30       30    0                                      KOCHIA          70      50       0     0                                      SNTLS CHAMOMILE 90      50       50    20                                     REDROOT PIGWEED 60      50       50    50                                     LADY SMARTWEED  100     100      100   0                                      PERSN SPEEDWELL 80      40       20    0                                      WILD BUCKWHEAT  0       0        0     0                                      MUSTARD SPP.    50      50       20    20                                     WILD RADISH     80      50       30    20                                     ANN. BLUEGRASS  80      50       50    20                                     ITALN. RYEGRASS 40      50       20    0                                      BLACKGRASS      50      30       0     0                                      GREEN FOXTAIL   50      50       30    30                                     WILD OATS       20      20       0     0                                      JET RAPE        30      0        0     0                                      PREEMERGENCE                                                                  PARK WHEAT      30                                                            BONANZA BARLEY  50                                                            BLACK NIGHTSHAD 0                                                             CMN CHICKWEED   20                                                            LAMBSQUARTER    85                                                            CTCHWD BEDSTRAW 0                                                             KOCHIA          100                                                           SNTLS CHAMOMILE 100                                                           REDROOT PIGWEED 80                                                            PERSN SPEEDWELL 50                                                            WILD BUCKWHEAT  30                                                            MUSTARD SPP.    0                                                             WILD RADISH     0                                                             ANN. BLUEGRASS  80                                                            ITALN. RYEGRASS 0                                                             BLACKGRASS      20                                                            GREEN FOXTAIL   100                                                           WILD OATS       20                                                            JET RAPE        20                                                            ______________________________________                                        CMPD 52                                                                                     RATE GM/HA                                                                    0500  0250     0125    0064                                     ______________________________________                                        POSTEMERGENCE                                                                 PARK WHEAT      50      40       30    30                                     BONANZA BARLEY  40      20       20    0                                      BLACK NIGHTSHAD 70      10       0     0                                      CMN CHICKWEED   0       0        0     0                                      LAMBSQUARTER    10      0        0     0                                      CTCHWD BEDSTRAW 100     70       80    20                                     KOCHIA          70      0        0     0                                      SNTLS CHAMOMILE 85      50       50    20                                     REDROOT PIGWEED 90      90       50    0                                      PERSN SPEEDWELL 90      60       30    40                                     WILD BUCKWHEAT  30      0        0     0                                      MUSTARD SPP.    50      20       0     0                                      WILD RADISH     80      50       10    10                                     ANN. BLUEGRASS  70      60       40    30                                     ITALN. RYEGRASS 80      50       20    0                                      BLACKGRASS      60      20       0     0                                      GREEN FOXTAIL   75      40       0     0                                      WILD OATS       30      20       0     0                                      JET RAPE        40      20       0     0                                      ______________________________________                                        CMPD 52                                                                                     RATE GM/HA                                                                    0250                                                            ______________________________________                                        PREEMERGENCE                                                                  PARK WHEAT      70                                                            BONANZA BARLEY  70                                                            BLACK NIGHTSHAD 100                                                           CMN CHICKWEED   0                                                             LAMBSQUARTER    100                                                           CTCHWD BEDSTRAW 100                                                           KOCHIA          0                                                             SNTLS CHAMOMILE 100                                                           REDROOT PIGWEED 100                                                           PERSN SPEEDWELL 100                                                           WILD BUCKWHEAT  20                                                            MUSTARD SPP.    50                                                            WILD RADISH     50                                                            ANN. BLUEGRASS  100                                                           ITALN. RYEGRASS 70                                                            BLACKGRASS      20                                                            GREEN FOXTAIL   100                                                           WILD OATS       70                                                            JET RAPE        20                                                            ______________________________________                                        CMPD 4                                                                                      RATE GM/HA                                                                    0500  0250     0125    0064                                     ______________________________________                                        POSTEMERGENCE                                                                 PARK WHEAT      50      30       10    0                                      BONANZA BARLEY  60      40       30    20                                     BLACK NIGHTSHAD 90      70       30    10                                     CMN CHICKWEED   0       0        0     0                                      LAMBSQUARTER    70      20       20    0                                      CTCHWD BEDSTRAW 100     80       20    20                                     KOCHIA          90      70       30    0                                      SNTLS CHAMOMILE 85      70       50    30                                     REDROOT PIGWEED 90      90       40    20                                     PERSN SPEEDWELL 100     100      70    20                                     WILD BUCKWHEAT  70      40       0     0                                      MUSTARD SPP.    80      40       40    20                                     WILD RADISH     90      80       60    20                                     ANN. BLUEGRASS  60      40       20    0                                      ITALN. RYEGRASS 80      30       0     0                                      BLACKGRASS      50      20       20    0                                      GREEN FOXTAIL   80      20       20    0                                      WILD OATS       30      0        0     0                                      JET RAPE        30      20       20    0                                      PREEMERGENCE                                                                  PARK WHEAT      80                                                            BONANZA BARLEY  80                                                            BLACK NIGHTSHAD 100                                                           CMN CHICKWEED   0                                                             LAMBSQUARTER    100                                                           CTCHWD BEDSTRAW 100                                                           KOCHIA          100                                                           SNTLS CHAMOMILE 100                                                           REDROOT PIGWEED 100                                                           LADY SMARTWEED  100                                                           PERSN SPEEDWELL 90                                                            WILD BUCKWHEAT  40                                                            MUSTARD SPP.    50                                                            WILD RADISH     50                                                            ANN. BLUEGRASS  100                                                           ITALN. RYEGRASS 70                                                            BLACKGRASS      90                                                            GREEN FOXTAIL   100                                                           WILD OATS       90                                                            JET RAPE        40                                                            ______________________________________                                        CMPD 107                                                                                    RATE GM/HA                                                                    0250                                                            ______________________________________                                        PREEMERGENCE                                                                  PARK WHEAT      30                                                            BONANZA BARLEY  30                                                            BLACK NIGHTSHAD 80                                                            CMN CHICKWEED   0                                                             LAMBSQUARTER    90                                                            CTCHWD BEDSTRAW 0                                                             KOCHIA          70                                                            SNTLS CHAMOMILE 70                                                            REDROOT PIGWEED 100                                                           PERSN SPEEDWELL 100                                                           WILD BUCKWHEAT  0                                                             MUSTARD SPP.    20                                                            WILD RADISH     60                                                            ANN. BLUEGRASS  20                                                            ITALN. RYEGRASS 0                                                             BLACKGRASS      20                                                            GREEN FOXTAIL   100                                                           WILD OATS       0                                                             JET RAPE        30                                                            ______________________________________                                    

TEST F

Weed species were planted 3 or 4 per 15-cm diameter pot in Sassafrassandy loam (pH 6.8; 1% OM). Cotton was planted separately in the samesized pot. Postemergence plantings were made 12-16 days prior totreating so plants were in the 2- to 3-leaf stage (5-12 cm tall).Preemergence plantings were made the day before treating. Compounds weresprayed in a suitable non-phytotoxic solvent at 374 1/ha, then after 3weeks of growth in a greenhouse, plant responses were visually rated ona percent scale where 0 =no injury and 100 =plant death. The followingspecies were included:

    ______________________________________                                                                     Planting Depth                                   Common Name  Latin Name      (cm)                                             ______________________________________                                        Cotton (Coker 315)                                                                         Gossypium hirsutum                                                                            2                                                Barnyardgrass                                                                              Echinochloa crus-galli                                                                        1                                                Bermudagrass Cynodon dactylon                                                                              1                                                Broadleaf signalgrass                                                                      Brachiaria platyphylla                                                                        1                                                Crabgrass    Digitaria sanguinalis                                                                         1                                                Fall panicum Panicum dichotomiflorum                                                                       1                                                Goosegrass   Eleusine indica 1                                                Johnsongrass Sorghum halepense                                                                             1                                                Nutsedge     Cyperus rotundus                                                                              3                                                Cocklebur    Xanthium pensylvanicum                                                                        3                                                Ivy leaf morningglory                                                                      Ipomoea hederacea                                                                             3                                                Lambsquarters                                                                              Chenopodium album                                                                             1                                                Pigweed      Amaranthus retroflexus                                                                        1                                                Prickly sida Sida spinosa    1                                                Purslane     Portulaca oleracea                                                                            1                                                Sicklepod    Cassia obtusifolia                                                                            3                                                Smartweed    Polygonum persicaria                                                                          1                                                Velvetleaf   Abutilon theophrasti                                                                          3                                                Ground cherry                                                                              Physalis heterophylla                                                                         1                                                ______________________________________                                    

The results are shown in Table F.

                  TABLE F                                                         ______________________________________                                        CMPD 4                                                                                     RATE GM/HA                                                                    0500  0250    0125    0064 0032                                  ______________________________________                                        PREEMERGENCE                                                                  COKER COTTON   0       0       0     0    0                                   REDROOT PIGWEED                                                                              100     100     60    70   50                                  LAMBSQUARTER   70      60      20    20   0                                   VELVETLEAF     30      0       0     0    0                                   PRICKLY SIDA   90      100     0     0    0                                   SICKLEPOD      0       0       0     0    0                                   COCKLEBUR      0       0       0     0    0                                   CMN PURSLANE   80      30      30    20   0                                   IVY MORNINGLORY                                                                              0       0       0     0    0                                   GOOSEGRASS     100     100     100   80   80                                  BERMUDAGRASS   100     100     95    20   0                                   BARNYARDGRASS  95      0       0     0    0                                   JOHNSONGRASS   50      50      20    0    0                                   FALL PANICUM   100     100     90    90   90                                  LARGE CRABGRASS                                                                              100     100     100   20   0                                   BRDLF SGNLGRASS                                                                              30      0       0     0    0                                   PURPLE NUTSEDGE                                                                              0       0       0     0    0                                   LADY SMARTWEED 20      20      0     0    0                                   GROUND CHERRY  0       0       0     0    0                                   ______________________________________                                    

What is claimed is:
 1. A compound of the formula: ##STR72## or apharmaceutically or agriculturally suitable salt thereof wherein E is anoxygen atom;A is perfluoroalkyl of 1-8 carbon atoms, N(CH₃)₂, OH,naphthyl optionally substituted with a total of 1-3 substituents each ofwhich is independently selected from halogen and CF₃, ##STR73##optionally substituted with 1 or 2 methyl groups, phenyl optionallysubstituted with a total of 1-3 substituents each of which isindependently selected from:halogen, alkyl of 1-4 carbon atoms,haloalkyl of 1-4 carbon atoms, alkoxy of 1-4 atoms, and with no morethan one group selected from:haloalkoxy of 1-4 carbon atoms, CN, CO₂R¹⁴, CH═NOR¹⁴, S(O)_(m) R⁵, R⁶, thereof, imidazol-1-yl,1,2,4-triazol-1-yl and ##STR74## optionally substituted with 1 or 2methyl groups, or a heterocycle selected from imidazol-1-yl,1,2,4-triazol-1-yl, 2- or 3-thienyl, and 2-, 3-, or 4-pyridyl or anN-oxide thereof optionally substituted with one or two substituents eachof which is independently selected from: halogen, alkyl of 1-4 carbonatoms, alkoxy of 1-4 carbon atoms, haloalkoxy of 1-4 carbon atoms, CF₃,and S(O)_(m) R⁵ ; B is alkyl of 1-8 carbon atoms, naphthyl, biphenyl,##STR75## perfluoroalkyl of 1-8 carbon atoms, phenyl optionallysubstituted with 1-3 substituents each of which is independentlyselected from:halogen, alkyl of 1-4 carbon atoms, haloalkyl of 1-4carbon atoms, alkoxy of 1-4 carbon atoms, and with no more than onegroup selected from haloalkoxy of 1-4 carbon atoms, CN, CO₂ R¹⁴,CH═NOR¹⁴, S(O)_(m) R⁵, 2-, 3-, or 4-pyridyl or an N-oxide thereof,benzyl optionally substituted on the phenyl ring with halogen or alkylof 1-4 carbon atoms, or optionally α-substituted with 1 or 2 methylgroups, or a heterocycle selected from 2- or 3-thienyl, and 2-, 3-, or4-pyridyl optionally substituted with one or two substituents each ofwhich is independently selected from:halogen, alkyl of 1-4 carbon atoms,haloalkoxy of 1-4 carbon atoms, CF₃ or S(O)_(m) R⁵ ; Q is H; L is CH; nis 0-4 with the proviso that when A is ##STR76## N(CH₃)₂, or OH, then nis other than O; m each occurrence is 0, 1 or 2; X is C, NR¹⁰, or O; Rand R¹ independently are H, alkyl of 1-4 carbon atoms, or phenyl, ortaken together form cycloalkyl of 3-7 carbon atoms; R² is H, allyl,propargyl, alkyl of 1-4 carbon atoms, ##STR77## or haloalkyl of 1-4carbon atoms; R³ and R⁴ independently are H, F, or alkyl of 1-4 carbonatoms; R⁵ is alkyl of 1-4 carbon atoms; R⁶ is phenyl optionallysubstituted with a total of 1-3 substituents each of which isindependently selected from halogen and CF₃ ; R⁷ is alkyl of 1-4 carbonatoms, phenyl, or benzyl; R⁸ and R⁹ independently are H, alkyl of 1-4carbon atoms, phenyl or benzyl; R¹⁰ is H, alkyl of 1-4 carbon atoms, oracetyl; and R¹⁴ is alkyl of 1-4 carbon atoms.
 2. A compound of claim 1wherein n is 0 or
 1. 3. A compound of claim 1 wherein R³ and R⁴ are eachindependently H, CH₃ or F.
 4. A compound of claim 1 wherein n is 0 or 1,and R³ and R⁴ are each independently H, CH₃ or F.
 5. A compound of claim4 wherein A and B independently are phenyl optionally substituted with atotal of 1-3 substituents (a) each of which is halogen, alkoxy of 1-4carbon atoms, alkyl of 1-4 carbon atoms, S(O)_(m) R⁵ or haloalkyl or 1-4carbon atoms, and (b) with no more than one 2-pyridyl substituent.
 6. Acompound of claim 5 wherein R and R¹ independently are H or CH₃.
 7. Acompound of claim 5 wherein n is
 0. 8. A compound of claim 5 wherein R²is H, alkyl of 1-4 carbon atoms, allyl or propargyl.
 9. A compound ofclaim 4 wherein R and R¹ independently are H or CH₃, R² is H, alkyl of1-4 carbon atoms, allyl or propargyl, n is 0, and A and B independentlyare phenyl optionally substituted with a total of 1-3 substituents (a)each of which is halogen, alkoxy of 1-4 carbon atoms, alkyl of 1-4carbon atoms, S(O)_(m) R⁵, or haloalkyl of 1-4 carbon atoms, and (b)with no more than one 2-pyridyl substituent.
 10. A compound of claim 9wherein R, R¹, R², R³, and R⁴ are all H.
 11. A compound of claim 9wherein A and B independently are phenyl optionally substituted with (a)halogen, CH₃, OCH₃, CF₃ or SCH₃, and (b) 2-pyridyl.
 12. A compound ofclaim 9 wherein R, R¹, R², R³, and R⁴ are all H, and A and Bindependently are phenyl optionally substituted with (a) halogen, CH₃OCH₃, CF₃ or SCH₃, and (b) 2-pyridyl.
 13. The compound of claim 1 whichis2-(2,4-difluorophenyl)-3-phenyl-1-(imidazol-1-yl)-3,4-epoxy-2-butanol,or a salt thereof.
 14. The compound of claim 1 which is2-(2-fluorophenyl)-3-(4-fluorophenyl)-1-(imidazol-1-yl)-3,4-epoxy-2-butanol,or a salt thereof.
 15. The compound of claim 1 which is2-(2,4-difluorophenyl)-3-(4-fluorophenyl)-1-(imidazol-1-yl)-3,4-epoxy-2-butanol,or a salt thereof.
 16. The compound of claim 1 which is2-(2,4-difluorophenyl)-3-(2-chlorophenyl)-1-(imidazol-1-yl)-3,4-epoxy-2-butanol,or a salt thereof.
 17. The compound of claim 1 which is2-(4-chlorophenyl)-1-(imidazol-1-yl)-3,4-epoxy-2-butanol, or a saltthereof.
 18. The compound of claim 1 which is2-phenyl-3-(2-trifluoromethylphenyl)-1-(imidazol-1-yl)-3,4-epoxy-2-butanol,or a salt thereof.
 19. The compound of claim 1 which is2-(2-chlorophenyl)-3-(2-chlorophenyl)-1-(imidazol-1-yl)-3,4-epoxy-2-butanol,or a salt thereof.
 20. The compound of claim 1 which is2-(2,4-difluorophenyl)-3-(4-(2-pyridyl)phenyl)-1-(imidazol-1-yl)-3,4-epoxy-2-butanol,or a salt thereof.
 21. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 1. 22. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 2. 23. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 3. 24. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 4. 25. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 5. 26. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 6. 27. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 7. 28. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 8. 29. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 9. 30. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 10. 31. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 11. 32. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 12. 33. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 13. 34. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 14. 35. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof the compound of claim
 15. 36. A pharmaceutical composition comprisinga suitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 16. 37. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 17. 38. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 18. 39. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 19. 40. A pharmaceutical composition comprising asuitable pharmaceutical carrier and a therapeutically effective amountof a compound of claim
 20. 41. An agricultural composition forcontrolling a plant fungus disease which comprises an effective amountof a compound of claim 1 and at least one of the following: surfactant,solid or liquid inert diluent.